Condensed bicyclic heterocyclic derivatives as pest control agents

ABSTRACT

The present invention relates to novel fused bicyclic heterocycle derivatives of formula (I)in which B1, B2, B3, B4, R1, R4, R5, R6 and n have the meanings mentioned above,to agrochemical formulations comprising the compounds of formula (I) and to their use as acaricides and/or insecticides for controlling animal pests, especially arthropods and in particular insects and arachnids.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is the National Stage entry of InternationalApplication No. PCT/EP2019/055823, filed 8 Mar. 2019, which claimspriority to European Patent Application No. 18161214.4, filed 12 Mar.2018.

BACKGROUND Field

The present invention relates to novel fused bicyclic heterocyclederivatives of the formula (I), to agrochemical formulations comprisingthe compounds of formula (I) and their use as acaricides and/orinsecticides for controlling animal pests, especially arthropods and inparticular insects and arachnids.

Description of Related Art

Fused bicyclic heterocycle derivatives having insecticidal propertieshave already been described in the literature, for example in WO2016/162318, WO 2016/129684, WO 2016/023954, WO 2016/142326, WO2016/169882, WO 2017/093180, WO 2017/061497, WO 2017/001311, WO2017/001314, WO 2017/084879, WO 2017/089190, WO 2017/133994, WO2017/155103, WO2018/033455, WO2018/050825, EP 17194731.0, EP18157886.5.

Modern insecticides and acaricides have to meet many demands, forexample in relation to extent, persistence and spectrum of their actionand possible use. Questions of toxicity, sparing of beneficial speciesand pollinators, environmental properties, soil degradability,application rates, combinability with other active compounds orformulation auxiliaries play a role, as does the question of thecomplexity involved in the synthesis of an active compound, andresistances can also occur, to mention just a few parameters. For allthese reasons alone, the search for novel crop protection compositionscannot be considered complete, and there is a constant need for novelcompounds having improved properties compared to the known compounds, atleast in relation to individual aspects.

SUMMARY

It was an object of the present invention to provide compounds for usefor controlling animal pests, which compounds widen the spectrum of thepesticides in various aspects.

Novel fused bicyclic heterocycle derivatives have now been found, thesehaving advantages over the compounds already known, examples of whichinclude better biological or environmental properties, optimum soildegradability, a wider range of application methods, better insecticidalor acaricidal action, and good compatibility with useful plants. Thefused bicyclic heterocycle derivatives can be used in combination withfurther agents for improving efficacy, especially against insects thatare difficult to control.

The subject matter of the present invention is therefore novel compoundsof formula (I)

in which (configuration 1)

-   B₁ represents C(R¹¹),-   B₂ represents C(R¹²),-   B₃ represents C(R¹³) and-   B₄ represents C(R¹⁴) and-   R¹ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyl,    (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl, amino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkyl-amino, (C₃-C₈)-cycloalkylamino,    (C₁-C₆)-alkylcarbonylamino, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl, alkylsulfonylamino,    aminosulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl or    di-(C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl,-   R¹¹, R¹², R¹³, R¹⁴ independently of one another represent hydrogen,    cyano, halogen, nitro, hydroxy, amino, SCN, tri-(C₁-C₆)-alkylsilyl,    (C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₃-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-halo alkynyl, (C₂-C₆)-cyanoalkynyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkythydroxyimino,    (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₃-C₆)-alkoxyimino,    (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,    (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₃-C₆)-alkylthio,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-alkylsulfinyl-(C₃-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,    (C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-haloalkylsulfonyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-alkylsulfonyl-(C₃-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,    (C₁-C₆)-alkylcarbonyl, (C₃-C₈)-cycloalkylcarbonyl,    (C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,    (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkyl    aminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, alkylaminosulfonyl,    (C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino) or NHCO—(C₃-C₈)-cycloalkyl    ((C₃-C₈)-cycloalkylcarbonylamino), or    -   represent aryl or hetaryl, each of which is optionally mono- or        polysubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, carboxyl, halogen, nitro, acetyl,        hydroxyl, amino, SCN, (C₃-C₈)-cycloalkyl,        (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,        (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,        (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, C₁-C₆)-cyano alkyl,        (C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₃-C₆)-alkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₃-C₆)-alkyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,        (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy,        (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,        (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,        (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,        (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkylsulfinyl,        (C₁-C₆)-alkoxy-(C₃-C₆)-alkylsulfinyl,        (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,        (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,        (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,        (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,        (C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,        (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminocarbonyl,        (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,        (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,        (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,        (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,        (C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,        (C₁-C₆)-alkylaminothiocarbonyl,        di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylamino,        (C₁-C₆)-alkylcarbonylamino,    -   where at most three of the radicals R¹¹, R¹², R¹³ and R¹⁴        represent a substituent different from hydrogen,-   R⁴, R⁵ independently of one another represent (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-halo    alkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl,    (C₂-C₄)-alkynyl, (C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkynyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl or    (C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl and-   R⁶ represents hydrogen, cyano, halogen, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₃-C₆)-cycloalkyl,    cyano-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylsulfinyl,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfonyl oxy,    (C₁-C₄)-alkylcarbonyl, (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl,    (C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,    (C₁-C₄)-alkylsulfonylamino, (C₁-C₄)-alkylamino,    di-(C₁-C₄)-alkylamino, aminosulfonyl, (C₁-C₄)-alkylaminosulfonyl or    di-(C₁-C₄)-alkylaminosulfonyl and-   n represents 0, 1 or 2.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

It has additionally been found that the compounds of formula (I) havevery good efficacy as pesticides, preferably as insecticides and/oracaricides, exhibit optimum soil degradability and additionallygenerally have very good plant compatibility, in particular with respectto crop plants.

The compounds according to the invention are defined in general terms bythe formula (I). Preferred substituents or ranges of the radicals givenin the formulae mentioned above and below are illustrated hereinafter:

Configuration 2

Compounds of formula (I)

-   B₁ preferably represents CH,-   B₂ preferably represents C(R¹²),-   B₃ preferably represents C(R¹³) and-   B₄ preferably represents CH and-   R¹ preferably represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-haloalkynyl, (C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl    or (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,-   R¹², R¹³ independently of one another preferably represent hydrogen,    cyano, halogen, hydroxy, amino, SCN, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,    (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,    (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,    (C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-haloalkylsulfonyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,    (C₁-C₆)-alkylcarbonyl, (C₃-C₈)-cycloalkylcarbonyl,    (C₁-C₆-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,    (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, amino sulfonyl,    (C₁-C₆)-alkylaminosulfonyl, alkylaminosulfonyl,    (C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino) or NHCO—(C₃-C₈)-cycloalkyl    ((C₃-C₈)-cycloalkylcarbonylamino), or    -   represent aryl or hetaryl, each of which is optionally mono- or        polysubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, carboxyl, halogen, acetyl, hydroxy,        amino, SCN, (C₃-C₈)-cycloalkyl,        (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,        (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,        (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,        (C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,        (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylsulfinyl,        (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl or        (C₁-C₆)-haloalkylsulfonyl,-   R⁴, R⁵ independently of one another preferably represent    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,    (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl or    halo-(C₃-C₆)-cycloalkyl,-   R⁶ preferably represents hydrogen, cyano, halogen, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₃-C₆)-cycloalkyl,    cyano-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl or    (C₁-C₄)-haloalkylsulfonyl and-   n preferably represents 0, 1 or 2.    Configuration 3    Compounds of Formula (I)-   B₁ particularly preferably represents CH,-   B₂ particularly preferably represents C(R¹²),-   B₃ particularly preferably represents C(R¹³) and-   B₄ particularly preferably represents CH and-   R¹ particularly preferably represents (C₁-C₆)-alkyl,    (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl or (C₃-C₈)-cycloalkyl,-   R¹², R¹³ independently of one another particularly preferably    represent hydrogen, cyano, halogen, hydroxy, amino, SCN,    (C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,    halo-(C₃-C₈)-cycloalkyl, cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl,    (C₁-C₆)-haloalkyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl,    (C₁-C₆)-cyanoalkyl, (C₁-C₆)-hydroxyalkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,    (C₁-C₆)-alkoxy, C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl,    (C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-haloalkylsulfonyl,    (C₁-C₆)-alkylcarbonyl, (C₃-C₈)-cycloalkylcarbonyl,    (C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkyl aminothiocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylamino,    di-(C₁-C₆)-alkylaminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,    di-(C₁-C₆)-alkylaminosulfonyl, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino) or NHCO—(C₃-C₈)-cycloalkyl    ((C₃-C₈)-cycloalkylcarbonylamino),-   R⁴, R⁵ independently of one another particularly preferably    represent (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl or    (C₃-C₆)-cycloalkyl,-   R⁶ particularly preferably represents hydrogen, cyano, halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl,    cyano-(C₃-C₆)-cycloakyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulfinyl or (C₁-C₄)-haloalkylsulfonyl and-   n particularly preferably represents 0, 1 or 2.    Configuration 4

In a very particularly preferred configuration of the compounds of theformula (I), the compounds of the formulae (Ia) are obtained.

Compounds of the Formula (Ia)

where

-   R¹ very particularly preferably represents (C₁-C₄)-alkyl or    (C₃-C₆)-cycloalkyl,-   R¹², R¹³ independently of one another very particularly preferably    represent hydrogen, cyano, halogen, hydroxy, (C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)cycloalkyl,    cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio,    (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl,    (C₁-C₆)-alkylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl,    (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkylcarbonyl,    (C₃-C₈)-cycloalkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylamino,    di-(C₁-C₆)-alkylamino, aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,    di-(C₁-C₆)-alkylaminosulfonyl, (C₃-C₈)-cycloalkylamino,    NHCO—(C₁-C₆)-alkyl ((C₁-C₆)-alkylcarbonylamino) or    NHCO—(C₃-C₈)-cycloalkyl ((C₃-C₈)-cycloalkylcarbonylamino),-   R⁴, R⁵ independently of one another very particularly preferably    represent (C₁-C₄)-alkyl or (C₃-C₆)-cycloalkyl,-   R⁶ very particularly preferably represents hydrogen, halogen,    (C₁-C₄)-haloalkyl, cyano-(C₃-C₆)-cycloalkyl, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl or    (C₁-C₄)-haloalkylsulfonyl and-   n very particularly preferably represents 0, 1 or 2.    Configuration 5    Compounds of the Formula (Ia)

where

-   R¹ with emphasis represents (C₁-C₄)-alkyl,-   R¹² with emphasis represents (C₁-C₄)-cyanoalkyl or    (C₃-C₆)-cycloalkyl which is optionally monosubstituted by cyano,-   R¹³ with emphasis represents hydrogen, R⁴, R⁵ independently of one    another with emphasis represent (C₁-C₄)-alkyl,-   R⁶ with emphasis represents (C₁-C₄)-haloalkyl and-   n with emphasis represents 2.    Configuration 6-1    Compounds of the Formula (Ia),

where

-   R¹ in particular represents ethyl,-   R¹² in particular represents cyanocyclopropyl,-   R¹³ in particular represents hydrogen,-   R⁴, R⁵ in particular represent methyl,-   R⁶ in particular represents trifluoromethyl and-   n in particular represents 2.    Configuration 6-2    Compounds of the Formula (Ia),

where

-   R¹ in particular represents ethyl,-   R¹² in particular represents cyanocyclopropyl, cyclopropyl or    cyanomethyl,-   R¹³ in particular represents hydrogen,-   R⁴, R⁵ in particular represent methyl,-   R⁶ in particular represents trifluoromethyl and-   n in particular represents 2.

Hereinbelow, the statements concerning the compounds of the formula (I)do, of course, also apply to the compounds of the formulae (Ia) and(Ia′) which are embraced by formula (I).

Hereinbelow, the term configuration 6 represents configuration 6-1 orconfiguration 6-2.

In a preferred embodiment, the invention relates to compounds of theformula (I) where

-   n represents 2 and

B₁, B₂, B₃, B₄, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have the meaningsdescribed in configuration (1) or configuration (2) or configuration (3)or configuration (4).

In a preferred embodiment, the invention relates to compounds of theformula (I) where

-   R¹ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl or    (C₃-C₈)-cycloalkyl and

B₁, B₂, B₃, B₄, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have the meaningsdescribed in configuration (1) or configuration (2) or configuration (4)or configuration (5) or configuration (6).

In a particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R¹ represents (C₁-C₄)-alkyl or (C₃-C₆)-cycloalkyl and

B₁, B₂, B₃, B₄, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have the meaningsdescribed in configuration (1) or configuration (2) or configuration (3)or configuration (5) or configuration (6).

In a very particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R¹ represents (C₁-C₄)-alkyl and

B₁, B₂, B₃, B₄, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have the meaningsdescribed in configuration (1) or configuration (2) or configuration (3)or configuration (4) or configuration (6).

In a most preferred embodiment, the invention relates to compounds ofthe formula (I) where

-   R¹ represents ethyl and

B₁, B₂, B₃, B₄, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have the meaningsdescribed in configuration (1) or configuration (2) or configuration (3)or configuration (4) or configuration (5).

In a preferred embodiment, the invention relates to compounds of theformula (I) where

-   R⁴ represents (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl or    (C₃-C₆)-cycloalkyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (4) or configuration (5) or configuration (6).

In a particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R⁴ represents (C₁-C₄)-alkyl or (C₃-C₆)-cycloalkyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (5) or configuration (6).

In a very particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R⁴ represents (C₁-C₄)-alkyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (6).

In a most preferred embodiment, the invention relates to compounds ofthe formula (I) where

-   R⁴ represents methyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5).

In a preferred embodiment, the invention relates to compounds of theformula (I) where

-   R⁵ represents (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl or    (C₃-C₆)-cycloalkyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (4) or configuration (5) or configuration (6).

In a particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R⁵ represents (C₁-C₄)-alkyl or (C₃-C₆)-cycloalkyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (5) or configuration (6).

In a very particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R⁵ represents (C₁-C₄)-alkyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (6).

In a most preferred embodiment, the invention relates to compounds ofthe formula (I) where

-   R⁵ represents methyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5).

In a preferred embodiment, the invention relates to compounds of theformula (I) where

-   R⁶ represents hydrogen, cyano, halogen, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, cyano-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl    or (C₁-C₄)-haloalkylsulfonyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (4) or configuration (5) or configuration (6).

In a particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R⁶ represents hydrogen, halogen, (C₁-C₄)-haloalkyl,    cyano-(C₃-C₆)-cycloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulfinyl or (C₁-C₄)-haloalkylsulfonyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R⁶, R¹¹, R¹², R¹³ and R¹⁴ have themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (5) or configuration (6).

In a very particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R⁶ represents (C₁-C₄)-haloalkyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R¹¹, R¹², R¹³ and R¹⁴ have the meaningsdescribed in configuration (1) or configuration (2) or configuration (3)or configuration (4) or configuration (6).

In a most preferred embodiment, the invention relates to compounds ofthe formula (I) where

-   R⁶ represents trifluoromethyl and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵, R¹¹, R¹², R¹³ and R¹⁴ have the meaningsdescribed in configuration (1) or configuration (2) or configuration (3)or configuration (4) or configuration (5).

In a preferred embodiment, the invention relates to compounds of theformula (I) where

-   R¹ represents (C₁-C₄)-alkyl,-   R⁴, R⁵ independently of one another represent (C₁-C₄)-alkyl or    (C₃-C₆)-cycloalkyl,-   R⁶ represents (C₁-C₄)-haloalkyl and

B₁, B₂, B₃, B₄, n, R¹¹, R¹², R¹³ and R¹⁴ have the meanings described inconfiguration (1) or configuration (2) or configuration (3) orconfiguration (4) or configuration (5) or configuration (6).

In a particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R¹, R⁴, R⁵ independently of one another represent C₁-C₄-alkyl,-   R⁶ represents (C₁-C₄)-haloalkyl and

B₁, B₂, B₃, B₄, n, R¹¹, R¹², R¹³ and R¹⁴ have the meanings described inconfiguration (1) or configuration (2) or configuration (3) orconfiguration (4) or configuration (5) or configuration (6).

In a very particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R¹ represents ethyl,-   R⁴ represents methyl,-   R⁵ represents methyl,-   R⁶ represents trifluoromethyl and

B₁, B₂, B₃, B₄, n, R¹¹, R¹², R¹³ and R¹⁴ have the meanings described inconfiguration (1) or configuration (2) or configuration (3) orconfiguration (4) or configuration (5).

In a preferred embodiment, the invention relates to compounds of theformula (I) where

-   R¹¹, R¹², R¹³ independently of one another represent hydrogen,    cyano, halogen, hydroxy, amino, SCN, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,    (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,    (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,    (C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-haloalkylsulfonyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,    (C₁-C₆)-alkylcarbonyl, (C₃-C₈)-cycloalkylcarbonyl,    (C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,    (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, amino sulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,    (C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino) or NHCO—(C₃-C₈)-cycloalkyl    ((C₃-C₈)-cycloalkylcarbonylamino), or    -   represent aryl or hetaryl, each of which is optionally mono- or        polysubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, carboxyl, halogen, acetyl, hydroxy,        amino, SCN, (C₃-C₈)-cycloalkyl,        (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,        (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-halo alkenyl,        (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,        (C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,        (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylsulfinyl,        (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl or        (C₁-C₆)-haloalkylsulfonyl,    -   where at most two of the radicals R¹¹, R¹² and R¹³ represent a        substituent different from hydrogen,-   R¹⁴ represents hydrogen and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵ and R⁶ have the meanings described inconfiguration (1) or configuration (3) or configuration (4) orconfiguration (5) or configuration (6).

In a particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R¹¹, R¹², R¹³ independently of one another represent hydrogen,    cyano, halogen, hydroxy, amino, SCN, (C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy,    (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy, (C₁-C₆)-alkylthio,    (C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulfinyl,    (C₁-C₆)-alkylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl,    (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkylcarbonyl,    (C₃-C₈)-cycloalkylcarbonyl, (C₁-C₆)-alkylthiocarbonyl,    (C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkoxycarbonyl,    (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkyl aminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylamino,    di-(C₁-C₆)-alkylamino, amino sulfonyl, (C₁-C₆)-alkylaminosulfonyl,    di-(C₁-C₆)-alkylaminosulfonyl, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkyl amino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino) or NHCO—(C₃-C₈)-cycloalkyl    ((C₃-C₈)-cycloalkylcarbonylamino),    where at most two of the radicals R¹¹, R¹² and R¹³ represent a    substituent different from hydrogen, represents hydrogen and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵ and R⁶ have the meanings described inconfiguration (1) or configuration (2) or configuration (4) orconfiguration (5) or configuration (6).

In a very particularly preferred embodiment, the invention relates tocompounds of the formula (I) where

-   R¹¹, R¹², R¹³ independently of one another represent hydrogen,    cyano, halogen, hydroxy, (C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)cycloalkyl,    cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-haloalkyl,    (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio,    (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl,    (C₁-C₆)-alkylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl,    (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkylcarbonyl,    (C₃-C₈)-cycloalkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylamino,    di-(C₁-C₆)-alkylamino, amino sulfonyl, (C₁-C₆)-alkyl aminosulfonyl,    di-(C₁-C₆)-alkylaminosulfonyl, (C₃-C₈)-cycloalkylamino,    NHCO—(C₁-C₆)-alkyl ((C₁-C₆)-alkylcarbonylamino) or    NHCO—(C₃-C₈)-cycloalkyl ((C₃-C₈)-cycloalkylcarbonylamino),    where at most two of the radicals R¹¹, R¹² and R¹³ represent a    substituent different from hydrogen and-   R¹⁴ represents hydrogen and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵ and R⁶ have the meanings described inconfiguration (1) or configuration (2) or configuration (3) orconfiguration (5) or configuration (6).

In a most preferred embodiment, the invention relates to compounds ofthe formula (I) where

-   R¹² represents (C₁-C₄)-cyanoalkyl or (C₃-C₆)-cycloalkyl which is    optionally monosubstituted by cyano,-   R¹¹, R¹³ and R¹⁴ represent hydrogen and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵ and R⁶ have the meanings described inconfiguration (1) or configuration (2) or configuration (3) orconfiguration (4) or configuration (6).

In a specially preferred embodiment, the invention relates to compoundsof the formula (I) where

-   R¹² represents cyanocyclopropyl, cyclopropyl or cyanomethyl,-   R¹¹, R¹³ and R¹⁴ represent hydrogen and

B₁, B₂, B₃, B₄, n, R¹, R⁴, R⁵ and R⁶ have the meanings described inconfiguration (1) or configuration (2) or configuration (3) orconfiguration (4) or configuration (5) or configuration (6).

Preferably, for the formulae (I) the following structures (Ia) result,

where R¹, R⁴, R⁵, R⁶, R¹², R¹³ and n have the meanings described inconfiguration (1) or configuration (2) or configuration (3) orconfiguration (4) or configuration (5) or configuration (6).

Particularly preferably, for the formulae (I) the following structures(Ia′) result,

where R⁵, R⁶, R¹², R¹³ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(2) or configuration (3) or configuration (4) or configuration (5) orconfiguration (6).

In a preferred embodiment of the invention, in the formulae (Ia) and(Ia′) R¹³ represents hydrogen.

Particular preference is given to compounds of the formula I(a) where

-   R¹ represents (C₁-C₀-alkyl or (C₃-C₆)-cycloalkyl, in particular    (C₁-C₀-alkyl,-   R¹² represents (C₁-C₄)-cyanoalkyl or (C₃-C₀)-cycloalkyl which is    optionally monosubstituted by cyano,-   R¹³ represents hydrogen,-   R⁴, R⁵ independently of one another represent (C₁-C₀-alkyl or    (C₃-C₆)-cycloalkyl, in particular (C₁-C₄)-alkyl,-   R⁶ represents (C₁-C₄)-haloalkyl and-   n represents 2.

Very particular preference is given to compounds of the formula I(a)where

-   R¹ represents ethyl,-   R¹² represents cyanocyclopropyl, cyclopropyl or cyanomethyl,-   R¹³ represents hydrogen,-   R⁴, R⁵ represent methyl,-   R⁶ represents trifluoromethyl and-   n represents 2.

By definition, unless stated otherwise, halogen is selected from thegroup of fluorine, chlorine, bromine and iodine, preferably in turn fromthe group of fluorine, chlorine and bromine.

In the context of the present invention, unless defined differentlyelsewhere, the term “alkyl”, either on its own or else in combinationwith further terms, for example haloalkyl, is understood to mean aradical of a saturated, aliphatic hydrocarbon group which has 1 to 12carbon atoms and may be branched or unbranched. Examples of C₁-C₁₂-alkylradicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl.

According to the invention, unless defined differently elsewhere, theterm “alkenyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkenylradical which has at least one double bond, for example vinyl, allyl,1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyland 1,4-hexadienyl.

According to the invention, unless defined differently elsewhere, theterm “alkynyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkynylradical which has at least one triple bond, for example ethynyl,1-propynyl and propargyl. The alkynyl radical may also contain at leastone double bond.

According to the invention, unless defined differently elsewhere, theterm “cycloalkyl”, either on its own or else in combination with furtherterms, is understood to mean a C₃-C₈-cycloalkyl radical, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl.

The term “alkoxy”, either on its own or else in combination with furtherterms, for example haloalkoxy, is understood in the present case to meanan O-alkyl radical, where the term “alkyl” is as defined above.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms may be identical ordifferent. Unless stated otherwise, optionally substituted radicals maybe mono- or polysubstituted, where the substituents in the case ofpolysubstitutions may be the same or different.

According to the invention, unless defined differently elsewhere, theterm “aryl” is understood to mean an aromatic radical having 6 to 14carbon atoms, preferably phenyl, naphthyl, anthryl or phenanthrenyl,more preferably phenyl.

Unless defined differently elsewhere, the term “arylalkyl” is understoodto mean a combination of the radicals “aryl” and “alkyl” defined inaccordance with the invention, where the radical is generally bonded viathe alkyl group; examples of these are benzyl, phenylethyl or-methylbenzyl, particular preference being given to benzyl.

Unless defined differently elsewhere, “hetaryl” denotes a mono-, bi- ortricyclic heterocyclic group of carbon atoms and at least oneheteroatom, where at least one cycle is aromatic. Preferably, thehetaryl group contains 3, 4, 5, 6, 7 or 8 carbon atoms and is selectedfrom the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl,imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl,1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl,pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl,indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl,benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole,quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl,quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl,imidazopyridinyl and indolizinyl.

Unless defined differently elsewhere, “heterocyclyl” denotes amonocyclic, saturated or partially saturated 4-, 5-, 6- or 7-memberedring of carbon atoms and at least one heteroatom in the ring.Preferably, the heterocyclyl group contains 3, 4, 5 or 6 carbon atomsand 1 or 2 heteroatoms from the group consisting of oxygen, sulfur andnitrogen. Examples of heterocyclyl are azetidinyl, azolidinyl, azinanyl,oxetanyl, oxolanyl, oxanyl, dioxanyl, thietanyl, thiolanyl, thianyl andtetrahydrofuryl.

Depending on the nature of the substituents, the compounds of formula(I) may be in the form of geometric and/or optically active isomers orcorresponding isomer mixtures in different compositions. Thesestereoisomers are, for example, enantiomers, diastereomers, atropisomersor geometric isomers. The invention therefore encompasses purestereoisomers and any desired mixtures of these isomers.

The compounds of formula (I) can also be present as salts, in particularacid addition salts and metal salt complexes. The compounds of theformula (I) and their acid addition salts and metal salt complexes havegood efficacy, especially for control of animal pests.

Suitable salts of the compounds of the general formula (I) includecustomary nontoxic salts, i.e. salts with appropriate bases and saltswith added acids. Preference is given to salts with inorganic bases,such as alkali metal salts, for example sodium, potassium or caesiumsalts, alkaline earth metal salts, for example calcium or magnesiumsalts, ammonium salts, salts with organic bases and with inorganicamines, for example triethylammonium, dicyclohexylammonium,N,N′-dibenzylethylenediammonium, pyridinium, picolinium orethanolammonium salts, salts with inorganic acids, for examplehydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates, orphosphates, salts with organic carboxylic acids or organic sulfonicacids, for example formates, acetates, trifluoroacetates, maleates,tartrates, methanesulfonates, benzenesulfonates orpara-toluenesulfonates, salts with basic amino acids, for examplearginates, aspartates or glutamates, and the like.

The radical definitions or illustrations given above in general terms orlisted within ranges of preference apply correspondingly to end productsand to starting materials and intermediates. These radical definitionscan be combined with one another as desired, i.e. including combinationsbetween the respective ranges of preference.

Preference according to the invention is given to using compounds offormula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to usingcompounds of formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to usingcompounds of formula (I) which contain a combination of the definitionslisted above as being very particularly preferred.

Emphasis according to the invention is given to using compounds offormula (I) which contain a combination of the meanings listed above asbeing emphasized.

Especially used according to the invention are compounds of formula (I)which contain a combination of the meanings listed above as beingspecial.

The compounds of formula (I) according to the invention can be obtainedby the processes shown in the following schemes:

Process A

Here, the variables B₁, B₂, B₃, B₄, R¹, R⁴, R⁵, R⁶ and n are defined asabove, in particular as described in configurations 1 to 6.

Step a)

The compounds of the formula (IV) can be prepared by the reaction ofcompounds of the formula (II) with carboxylic acids of the formula (III)in the presence of a condensing agent or a base.

Compounds of the formula (II) can be prepared by the processes describedin WO2016/023954. Carboxylic acids of the formula (III) can be preparedby the processes published in WO2016/162318. Further processes for thepreparation of carboxylic acids (III) are described in processes B andC.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (III) can be carried out neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogenous compounds,for example pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI),1,3-dicyclohexylcarbodiimide, thionyl chloride or oxalyl chloride.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andbicarbonates of alkali metals or alkaline earth metals. Particularpreference is given here to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium bicarbonate, potassium bicarbonate. Further suitable bases arealkali metal hydrides, for example sodium hydride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure and at temperatures of 0° C. to 180°C.; with preference, the reaction is carried out at atmospheric pressureand temperatures of 20 to 140° C.

Step b)

The compounds of the formula (I) can be prepared by condensing thecompounds of the formula (IV), for example analogously to the processesdescribed in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629,WO2012/086848, WO2013/018928, WO2015/000715 or WO 2015/121136.

The conversion to compounds of the formula (IV) can be carried out neator in a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogenous compounds, for example pyridine.

The reaction can be carried out in the presence of a condensing agent,an acid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulfonic acids such as para-toluenesulfonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogenous heterocycles such aspyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene(DBU); tertiary amines such as triethylamine andN,N-diisopropylethylamine; inorganic bases such as potassium phosphate,potassium carbonate and sodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Process B

Here, the variables B₁, B₂, B₃, B₄, R′, R⁴, R⁵, R⁶ and n are defined asabove, in particular as described in configurations 1 to 6. Here, X¹represents Cl, Br or I and M represents Na, K or Li.

Step a)

The compounds of the formula (XXVI) can be prepared by the reaction ofcompounds of the formula (II) with carboxylic acids of the formula (XXV)in the presence of a condensing agent or a base.

Compounds of the formula (II) can be prepared by the processes describedin WO2016/023954. Carboxylic acids of the formula (XXV) are eithercommercially available or can be prepared by known methods. A method ofpreparation is described in Process F.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (XXV) can be carried out neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogenous compounds,for example pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI),1,3-dicyclohexylcarbodiimide, thionyl chloride or oxalyl chloride.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andbicarbonates of alkali metals or alkaline earth metals. Particularpreference is given here to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium bicarbonate, potassium bicarbonate. Further suitable bases arealkali metal hydrides, for example sodium hydride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure and at temperatures of 0° C. to 180°C.; with preference, the reaction is carried out at atmospheric pressureand temperatures of 20 to 140° C.

Step b)

The compounds of the formula (XXVII) can be prepared by condensing thecompounds of the formula (XXVI), for example analogously to theprocesses described in WO2009/131237, WO2010/125985, WO2011/043404,WO2011/040629, WO2012/086848, WO2013/018928, WO2015/000715 or WO2015/121136.

The conversion to compounds of the formula (XXVII) can be carried outneat or in a solvent, preference being given to conducting the reactionin a solvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogenous compounds, for example pyridine.

The reaction can be carried out in the presence of a condensing agent,an acid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulfonic acids such as para-toluenesulfonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogenous heterocycles such aspyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene(DBU); tertiary amines such as triethylamine andN,N-diisopropylethylamine; inorganic bases such as potassium phosphate,potassium carbonate and sodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

Compounds of formula (XXVIII) can be prepared, for example analogouslyto the processes described in Journal of Organic Chemistry 2005, 70,2696-2700, by halogen/sulfone exchange starting with compounds offormula (XXVII) using a compound of formula (XXIII) in the presence of acopper source.

Compounds of formula (XXIII) are either commercially available or can beprepared by known methods, for example analogously to the processesdescribed in Tetrahedron Letters, 2014, 55, 3851-3855.

The reaction of the compound of formula (XXVII) with the compound offormula (XXIII) and the copper source is generally carried out in asolvent. Preference is given to using polar aprotic solvents, forexample dimethyl sulfoxide and N,N-dimethylformamide.

In most cases, the copper source used is CuBr, CuI or Cu(OAc)₂.

Examples of suitable sulfur reagents are sodium salts of sulfinic acids.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 20° C. ° C.to 200° C.

Process C

Carboxylic acids of the formula (XXV) are either commercially availableor can be prepared by known methods, for example from pyridines of theformula (XXIX) analogously to the processes described in WO2011/15343,WO2014/14874 or WO2010/34738.

Here, the variables B₁, B₂, B₃ and B₄ are defined as above, inparticular as described in configurations 1 to 6. Here, X represents Cl,Br or I, X¹ represents Cl, Br or I and R⁸ represents (C₁-C₄)-alkyl.

Step a)

Analogously to the processes described in WO2011/15343, WO2014/14874 orWO2010/34738, the compounds of the formula (XXX) can be converted byreaction of compounds of the formula (XXIX) withhydroxylamine-O-sulfonic acid in the presence of a base such as, forexample, potassium carbonate into an N-iminopyridinium intermediatewhich, in a second step, is converted in the presence of an acid suchas, for example, hydriodic acid (HI) in a suitable solvent such as, forexample, ethanol into the 1-aminopyridinium derivative of the formula(XXX). The pyridine derivatives of the formula (XXIX) are commerciallyavailable.

Step b) and c)

Analogously to the processes described in WO2011/15343, WO2014/14874 orWO2010/34738, compounds of the formula (XXXII) can be prepared fromcompounds of the formula (XXX) in a 1,3-dipolar cycloaddition with analkyne of the formula (XXXI). If isomers are formed, these can beseparated into the individual isomers by chromatographic methods. Inthis manner, it is possible to obtain the diester of the formula (XXXII)isometrically pure. By heating in a suitable acid such as, for example,aqueous sulfuric acid, compounds of the formula (XXXII) can be convertedby decarboxylation and simultaneous hydrolysis of the ester functioninto acids of the formula (XXXIII).

Step d)

By standard processes, compounds of the formula (XXV) can be prepared byhalogenation, for example analogously to the processes described inWO2011/50284 or WO2016/12896, using, for example, N-chlorosuccinimide orN-bromosuccinimide as halogenating agent in a suitable solvent such as,for example, dichloromethane or 1,2-dichloroethane.

Process D

In a further process, carboxylic acids of the formula (XXV) can beprepared from 2-formylpyridine derivatives of the formula (XXXV)analogously to the processes described in Journal of Medicinal Chemistry56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 or WO2009/29625.

Here, the variables B₁, B₂, B₃ and B₄ are defined as above, inparticular as described in configurations 1 to 6. Here, R⁹ represents(C₁-C₄)-alkyl and X¹ represents Cl, Br or I.

Step a)

Analogously to the processes described in Journal of Medicinal Chemistry56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 or WO2009/29625,the compounds of the formula (XXXVII) can be prepared by reaction ofcompounds of the formula (XXXV) with an alkyl azidoacetate derivative ofthe formula (XXXVI) in the presence of a suitable base such as, forexample, sodium methoxide in a suitable solvent such as, for example,methanol. The compounds of the formula (XXXV) are commercially availableor can be prepared by standard processes.

Step b)

Analogously to the processes described in Journal of Medicinal Chemistry56 (2013), 9635-9645, Synthesis 16 (2005), 2751-2757 or WO2009/29625,compounds of the formula (XXXVIII) can be prepared by cyclisation ofcompounds of the formula (XXXVII) in a suitable solvent such as, forexample, xylene. The reaction can be carried out under reduced pressure,at atmospheric pressure or under superatmospheric pressure and atelevated temperatures. Preference is given to a temperature above 100°C.

Step c, d)

Using standard methods, the ester of the formula (XXXVIII) can beconverted into the acid of the formula (XXXIII), using, for example, analkali metal hydroxide such as sodium hydroxide or lithium hydroxide asbase in an alcohol such as, for example, ethanol or a mixture oftetrahydrofuran and water as solvent.

Further conversion into compounds of the formula (XXV) is carried out bystandard processes via halogenation analogously to process C.

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of formula (I) are allowed to act on animal pests and/ortheir habitat. The control of the animal pests is preferably conductedin agriculture and forestry, and in material protection. This preferablyexcludes methods for surgical or therapeutic treatment of the human oranimal body and diagnostic methods carried out on the human or animalbody.

The invention further relates to the use of the compounds of formula (I)as pesticides, especially crop protection agents.

In the context of the present application, the term “pesticides” in eachcase also always encompasses the term “crop protection agents”.

The compounds of formula (I), given good plant tolerance, favorableendotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs against biotic and abiotic stressfactors, for increasing harvest yields, for improving the quality of theharvested material and for controlling animal pests, especially insects,arachnids, helminths, especially nematodes and molluscs, which areencountered in agriculture, in horticulture, in animal husbandry, inaquatic cultures, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector.

In the context of the present patent application, the term “hygiene”should be understood to mean any and all measures, provisions andprocedures which have the aim of preventing diseases, especiallyinfection diseases, and which serve to protect the health of humans andanimals and/or protect the environment and/or maintain cleanliness.According to the invention, this especially includes measures forcleaning, disinfection and sterilization, for example of textiles orhard surfaces, especially surfaces made of glass, wood, cement,porcelain, ceramic, plastic or else metal(s), in order to ensure thatthese are free of hygiene pests and/or their secretions. The scope ofprotection of the invention in this regard preferably excludes surgicalor therapeutic treatment procedures to be applied to the human body orthe bodies of animals, and diagnostic procedures which are conducted onthe human body or the bodies of animals.

The term “hygiene sector” covers all areas, technical fields andindustrial applications in which these hygiene measures, provisions andprocedures are important, for example with regard to hygiene inkitchens, bakeries, airports, bathrooms, swimming pools, departmentstores, hotels, hospitals, stables, animal keeping, etc.

The term “hygiene pest” should therefore be understood to mean one ormore animal pests whose presence in the hygiene sector is problematic,especially for reasons of health. A main aim is therefore that ofavoiding, or limiting to a minimum degree, the presence of hygiene pestsand/or the exposure to these in the hygiene sector. This can especiallybe achieved through the use of a pesticide which can be used both forprevention of infestation and for prevention of an existing infestation.It is also possible to use formulations which prevent or reduce exposureto pests. Hygiene pests include, for example, the organisms mentionedbelow.

The term “hygiene protection” thus covers all acts by which thesehygiene measures, provisions and procedures are maintained and/orimproved.

The compounds of formula (I) can preferably be used as pesticides. Theyare active against normally sensitive and resistant species and alsoagainst all or specific stages of development. The abovementioned pestsinclude:

pests from the phylum of the Arthropoda, especially from the class ofthe Arachnida e.g. Acarus spp., e.g. Acarus siro, Aceria kuko, Aceriasheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculusschlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp.,Boophilus spp., Brevipalpus spp., e.g. Brevipalpus phoenicis, Bryobiagraminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp.,Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoidesfarinae, Dermacentor spp., Eotetranychus spp., e.g. Eotetranychushicoriae, Epitrimerus pyri, Eutetranychus spp., e.g. Eutetranychusbanksi, Eriophyes spp., e.g. Eriophyes pyri, Glycyphagus domesticus,Halotydeus destructor, Hemitarsonemus spp., e.g. Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., e.g. Oligonychus coffeae, Oligonychus coniferarum,Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus,Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi,Ornithodorus spp., Ornithonyssus spp., Panonychus spp., e.g. Panonychuscitri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., e.g. Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., e.g. Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici;

from the class of the Chilopoda e.g. Geophilus spp., Scutigera spp.;

from the order or the class of the Collembola e.g. Onychiurus armatus;Sminthurus viridis;

from the class of the Diplopoda e.g. Blaniulus guttulatus;

from the class of the Insecta, for example from the order of Blattodeae.g. Blatta orientalis, Blattella asahinai, Blattella germanica,Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia,Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g. Periplanetaamericana, Periplaneta australasiae, Pycnoscelus surinamensis, Supellalongipalpa;from the order of the Coleoptera e.g. Acalymma vittatum, Acanthoscelidesobtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp.,e.g. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilusanxius, Agriotes spp., e.g. Agriotes linneatus, Agriotes mancus,Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum,Anoplophora spp., e.g. Anoplophora glabripennis, Anthonomus spp., e.g.Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomariaspp., e.g. Atomaria linearis, Attagenus spp., Bans caerulescens,Bruchidius obtectus, Bruchus spp., e.g. Bruchus pisorum, Bruchusrufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., e.g.Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchusrapae, Chaetocnema spp., e.g. Chaetocnema confinis, Chaetocnemadenticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp.,Cosmopolites spp., e.g. Cosmopolites sordidus, Costelytra zealandica,Ctenicera spp., Curculio spp., e.g. Curculio caryae, Curculiocaryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus,Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchusmangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus,Cylindrocopturus furnissi, Dendroctonus spp., e.g. Dendroctonusponderosae, Dermestes spp., Diabrotica spp., e.g. Diabrotica balteata,Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabroticaundecimpunctata undecimpunctata, Diabrotica virgifera virgifera,Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera,Diloboderus spp., Epicaerus spp., Epilachna spp., e.g. Epilachnaborealis, Epilachna varivestis, Epitrix spp., e.g. Epitrix cucumeris,Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrixtuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus,Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorphaelegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus,Hypothenemus spp., e.g. Hypothenemus hampei, Hypothenemus obscurus,Hypothenemus pubescens, Lachnosterna consanguinea, Lasiodermaserricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsadecemlineata, Leucoptera spp., e.g. Leucoptera coffeella, Limoniusectypus, Lissorhoptrus oryzophilus, Listronotus (=Hyperodes) spp., Lixusspp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllenespp., e.g. Megacyllene robiniae, Megascelis spp., Melanotus spp., e.g.Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., e.g.Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactusxanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus,Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae,Otiorhynchus spp., e.g. Otiorhynchus cribricollis, Otiorhynchusligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus,Otiorhynchus sulcatus, Oulema spp., e.g. Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Phyllophaga helleri, Phyllotreta spp., e.g. Phyllotreta armoraciae,Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popilliajaponica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp.,e.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodespunctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica,Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum,Scolytus spp., e.g. Scolytus multistriatus, Sinoxylon perforans,Sitophilus spp., e.g. Sitophilus granarius, Sitophilus linearis,Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobiumpaniceum, Sternechus spp., e.g. Sternechus paludatus, Symphyletes spp.,Tanymecus spp., e.g. Tanymecus dilaticollis, Tanymecus indicus,Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus,Tribolium spp., e.g. Tribolium audax, Tribolium castaneum, Triboliumconfusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.,e.g. Zabrus tenebrioides;from the order of the Dermaptera e.g. Anisolabis maritime, Forficulaauricularia, Labidura riparia;from the order of the Diptera e.g. Aedes spp., e.g. Aedes aegypti, Aedesalbopictus, Aedes sticticus, Aedes vexans, Agromyza spp., e.g. Agromyzafrontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., e.g.Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp.,Bactrocera spp., e.g. Bactrocera cucurbitae, Bactrocera dorsalis,Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala,Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp.,Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp.,e.g. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora,Contarinia schulzi, Contarinia sorghicola, Contarinia tritici,Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., e.g. Culexpipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp.,Cuterebra spp., Dacus oleae, Dasineura spp., e.g. Dasineura brassicae,Delia spp., e.g. Delia antiqua, Delia coarctata, Delia florilega, Deliaplatura, Delia radicum, Dermatobia hominis, Drosophila spp., e.g.Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleiaheraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopotaspp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp.,Hypoderma spp., Liriomyza spp., e.g. Liriomyza brassicae, Liriomyzahuidobrensis, Liriomyza sativae, Lucilia spp., e.g. Lucilia cuprina,Lutzomyia spp., Mansonia spp., Musca spp., e.g. Musca domestica, Muscadomestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp.,Paralauterborniella subcincta, Pegomya oder Pegomyia spp., e.g. Pegomyabetae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbiaspp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosisspp., Psila rosae, Rhagoletis spp., e.g. Rhagoletis cingulata,Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens,Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp.,e.g. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp.,Tipula spp., e.g. Tipula paludosa, Tipula simplex, Toxotrypanacurvicauda;from the order of the Hemiptera e.g. Acizzia acaciaebaileyanae, Acizziadodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., e.g.Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp.,Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis,Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., e.g.Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp.,e.g. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata,Aphanostigma pini, Aphis spp., e.g. Aphis citricola, Aphis craccivora,Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphishederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphisnerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridiaapicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., e.g.Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci,Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudushelichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp.,e.g. Cacopsylla pyricola, Calligypona marginata, Capulinia spp.,Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastesspp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii,Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,e.g. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum,Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp.,Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorinacitri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp.,Dysaphis spp., e.g. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphistulipae, Dysmicoccus spp., Empoasca spp., e.g. Empoasca abrupta,Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi,Eriosoma spp., e.g. Eriosoma americanum, Eriosoma lanigerum, Eriosomapyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp.,Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica,Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsyllaspinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopteruspruni, Icerya spp., e.g. Icerya purchasi, Idiocerus spp., Idioscopusspp., Laodelphax striatellus, Lecanium spp., e.g. Lecanium corni(=Parthenolecanium corni), Lepidosaphes spp., e.g. Lepidosaphes ulmi,Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula,Macrosiphum spp., e.g. Macrosiphum euphorbiae, Macrosiphum lilii,Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphissacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum,Monellia costalis, Monelliopsis pecanis, Myzus spp., e.g. Myzusascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzuspersicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp.,Nephotettix spp., e.g. Nephotettix cincticeps, Nephotettix nigropictus,Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Ortheziapraelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae,Paratrioza spp., e.g. Paratrioza cockerelli, Parlatoria spp., Pemphigusspp., e.g. Pemphigus bursarius, Pemphigus populivenae, Peregrinusmaidis, Perkinsiella spp., Phenacoccus spp., e.g. Phenacoccusmadeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp.,e.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspisaspidistrae, Planococcus spp., e.g. Planococcus citri, Prosopidopsyllaflava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona,Pseudococcus spp., e.g. Pseudococcus calceolariae, Pseudococcuscomstocki, Pseudococcus longispinus, Pseudococcus maritimus,Pseudococcus viburni, Psyllopsis spp., Psylla spp., e.g. Psylla buxi,Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrillaspp., Quadraspidiotus spp., e.g. Quadraspidiotus juglansregiae,Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesadagigas, Rastrococcus spp., Rhopalosiphum spp., e.g. Rhopalosiphum maidis,Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphumrufiabdominale, Saissetia spp., e.g. Saissetia coffeae, Saissetiamiranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus,Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobionavenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephalafestina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephelaspp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., e.g.Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum,Trioza spp., e.g. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteusvitifolii, Zygina spp.;from the suborder of the Heteroptera e.g. Aelia spp., Anasa tristis,Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylommalivida, Cavelerius spp., Cimex spp., e.g. Cimex adjunctus, Cimexhemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., e.g. Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp.,Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis,Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., e.g.Lygocoris pabulinus, Lygus spp., e.g. Lygus elisus, Lygus hesperus,Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae,Monalonion atratum, Nezara spp., e.g. Nezara viridula, Nysius spp.,Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., e.g.Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp.,Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp.,Stephanitis nashi, Tibraca spp., Triatoma spp.;from the order of the Hymenoptera e.g. Acromyrmex spp., Athalia spp.,e.g. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp.,Diprion spp., e.g. Diprion similis, Hoplocampa spp., e.g. Hoplocampacookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex)humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp.,Plagiolepis spp., Sirex spp., e.g. Sirex noctilio, Solenopsis invicta,Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., e.g.Vespa crabro, Wasmannia auropunctata, Xeris spp.;from the order of the Isopoda e.g. Armadillidium vulgare, Oniscusasellus, Porcellio scaber;from the order of the Isoptera e.g. Coptotermes spp., e.g. Coptotermesformosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp.,Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermesspp., Porotermes spp., Reticulitermes spp., e.g. Reticulitermesflavipes, Reticulitermes hesperus;from the order of the Lepidoptera e.g. Achroia grisella, Acronictamajor, Adoxophyes spp., e.g. Adoxophyes orana, Aedia leucomelas, Agrotisspp., e.g. Agrotis segetum, Agrotis ipsilon, Alabama spp., e.g. Alabamaargillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., e.g.Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathrabrassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella,Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora,Capua reticulana, Carpocapsa pomonella, Carposina niponensis,Cheimatobia brumata, Chilo spp., e.g. Chilo plejadellus, Chilosuppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixischalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocismedinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp.,Copitarsia spp., Cydia spp., e.g. Cydia nigricana, Cydia pomonella,Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis,Dioryctria spp., e.g. Dioryctria zimmermani, Earias spp., Ecdytolophaaurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp.,e.g. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyaspostvittana, Erannis spp., Erschoviella musculana, Etiella spp.,Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., e.g.Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella,Gracillaria spp., Grapholitha spp., e.g. Grapholita molesta, Grapholitaprunivora, Hedylepta spp., Helicoverpa spp., e.g. Helicoverpa armigera,Helicoverpa zea, Heliothis spp., e.g. Heliothis virescens, Hofmannophilapseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella,Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresiamolesta, Leucinodes orbonalis, Leucoptera spp., e.g. Leucopteracoffeella, Lithocolletis spp., e.g. Lithocolletis blancardella,Lithophane antennata, Lobesia spp., e.g. Lobesia botrana, Loxagrotisalbicosta, Lymantria spp., e.g. Lymantria dispar, Lyonetia spp., e.g.Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestrabrassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimnaseparata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisaspp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., e.g.Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp.,e.g. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp.,e.g. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycterspp., e.g. Phyllonorycter blancardella, Phyllonorycter crataegella,Pieris spp., e.g. Pieris rapae, Platynota stultana, Plodiainterpunctella, Plusia spp., Plutella xylostella (=Plutellamaculipennis), Podesia spp., e.g. Podesia syringae, Prays spp., Prodeniaspp., Protoparce spp., Pseudaletia spp., e.g. Pseudaletia unipuncta,Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobiusspp., e.g. Schoenobius bipunctifer, Scirpophaga spp., e.g. Scirpophagainnotata, Scotia segetum, Sesamia spp., e.g. Sesamia inferens,Sparganothis spp., Spodoptera spp., e.g. Spodoptera eradiana, Spodopteraexigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp.,Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Teciasolanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella,Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophagatapetzella, Trichoplusia spp., e.g. Trichoplusia ni, Tryporyzaincertulas, Tuta absoluta, Virachola spp.;from the order of the Orthoptera or Saltatoria e.g. Acheta domesticus,Dichroplus spp., Gryllotalpa spp., e.g. Gryllotalpa gryllotalpa,Hieroglyphus spp., Locusta spp., e.g. Locusta migratoria, Melanoplusspp., e.g. Melanoplus devastator, Paratlanticus ussuriensis,Schistocerca gregaria;from the order of the Phthiraptera e.g. Damalinia spp., Haematopinusspp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthiruspubis, Trichodectes spp.;from the order of the Psocoptera e.g. Lepinotus spp., Liposcelis spp.;from the order of the Siphonaptera e.g. Ceratophyllus spp.,Ctenocephalides spp., e.g. Ctenocephalides canis, Ctenocephalides felis,Pulex irritans, Tunga penetrans, Xenopsylla cheopis;from the order of the Thysanoptera e.g. Anaphothrips obscurus,Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri,Enneothrips flavens, Frankliniella spp., e.g. Frankliniella fusca,Frankliniella occidentalis, Frankliniella schultzei, Frankliniellatritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothripsspp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp.,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi,Thrips spp., e.g. Thrips palmi, Thrips tabaci;from the order of the Zygentoma (=Thysanura), e.g. Ctenolepisma spp.,Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;from the class of the Symphyla e.g. Scutigerella spp., e.g. Scutigerellaimmaculata;pests from the phylum of the Mollusca, for example from the class of theBivalvia, e.g. Dreissena spp.;and from the class of the Gastropoda e.g. B. Anion spp., e.g. Anion aterrufus, Biomphalaria spp., Bulinus spp., Deroceras spp., e.g. Deroceraslaeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp.,Succinea spp.;plant pests from the phylum of the Nematoda, i.e. phytoparasiticnematodes, in particular Aglenchus spp., e.g. Aglenchus agricola,Anguina spp., e.g. Anguina tritici, Aphelenchoides spp., e.g.Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp.,e.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimusnortoni, Bursaphelenchus spp., e.g. Bursaphelenchus cocophilus,Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp.,e.g. Cacopaurus pestis, Criconemella spp., e.g. Criconemella curvata,Criconemella onoensis, Criconemella ornata, Criconemella rusium,Criconemella xenoplax (=Mesocriconema xenoplax), Criconemoides spp.,e.g. Criconemoides ferniae, Criconemoides onoense, Criconemoidesornatum, Ditylenchus spp., e.g. Ditylenchus dipsaci, Dolichodorus spp.,Globodera spp., e.g. Globodera pallida, Globodera rostochiensis,Helicotylenchus spp., e.g. Helicotylenchus dihystera, Hemicriconemoidesspp., Hemicycliophora spp., Heterodera spp., e.g. Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hirschmaniella spp.,Hoplolaimus spp., Longidorus spp., e.g. Longidorus africanus,Meloidogyne spp., e.g. Meloidogyne chitwoodi, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp.,Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp.,Paratrichodorus spp., e.g. Paratrichodorus minor, Paratylenchus spp.,Pratylenchus spp., e.g. Pratylenchus penetrans, Pseudohalenchus spp.,Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp.,e.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp.,Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp.,e.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp.,e.g. Tylenchorhynchus annulatus, Tylenchulus spp., e.g. Tylenchulussemipenetrans, Xiphinema spp., e.g. Xiphinema index.

The compounds of formula (I) can, as the case may be, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). They can, as the case may be, also be used as intermediatesor precursors for the synthesis of other active compounds.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of formula (I). Optionally,the use forms comprise further pesticides and/or adjuvants which improveaction, such as penetrants, e.g. vegetable oils, for example rapeseedoil, sunflower oil, mineral oils, for example paraffin oils, alkylesters of vegetable fatty acids, for example rapeseed oil methyl esteror soya oil methyl ester, or alkanol alkoxylates and/or spreaders, forexample alkylsiloxanes and/or salts, for example organic or inorganicammonium or phosphonium salts, for example ammonium sulfate ordiammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulfosuccinate or hydroxypropylguar polymers and/or humectants,for example glycerol and/or fertilizers, for example ammonium-,potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of formula (I), optionally comprisefurther active agrochemical ingredients.

Preference is given to formulations or use forms comprising auxiliaries,for example extenders, solvents, spontaneity promoters, carriers,emulsifiers, dispersants, frost protection agents, biocides, thickenersand/or further auxiliaries, for example adjuvants. An adjuvant in thiscontext is a component which enhances the biological effect offormulation, without the component itself having any biological effect.Examples of adjuvants are agents which promote retention, spreading,attachment to the leaf surface or penetration.

These formulations are produced in a known manner, for example by mixingthe compounds of formula (I) with auxiliaries, for example extenders,solvents and/or solid carriers and/or other auxiliaries, for examplesurfactants. The formulations are produced either in suitable facilitiesor else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of formula (I), or tothe use forms prepared from these formulations (for example ready-to-usepesticides such as spray liquors or seed-dressing products).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), the esters (including fats andoils) and (poly)ethers, the simple and substituted amines, amides,lactams (such as N-alkylpyrrolidones) and lactones, the sulfones andsulfoxides (such as dimethyl sulfoxide), the carbonates and thenitriles.

If the extender utilized is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsare essentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide or dimethyl sulfoxide, carbonatessuch as propylene carbonate, butylene carbonate, diethyl carbonate ordibutyl carbonate, or nitriles such as acetonitrile or propanenitrile.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, for example xylene, tolueneor alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, for example chlorobenzene, chloroethylene or methylenechloride, aliphatic hydrocarbons, for example cyclohexane, paraffins,petroleum fractions, mineral and vegetable oils, alcohols, for examplemethanol, ethanol, isopropanol, butanol or glycol and their ethers andesters, ketones, for example acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents such asdimethyl sulfoxide, carbonates such as propylene carbonate, butylenecarbonate, diethyl carbonate or dibutyl carbonate, nitriles such asacetonitrile or propanenitrile, and also water.

In principle, it is possible to use all suitable carriers. Suitablecarriers include more particularly the following: for example ammoniumsalts and natural, finely ground rocks, such as kaolins, aluminas, talc,chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, andsynthetic, finely ground rocks, such as finely divided silica, aluminumoxide and natural or synthetic silicates, resins, waxes and/or solidfertilizers. It is likewise possible to use mixtures of such carriers.Useful carriers for granules include: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepiolite,dolomite, and synthetic granules of inorganic and organic flours, andalso granules of organic material such as sawdust, paper, coconutshells, maize cobs and tobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable extenders or carriers are those which are gaseous atstandard temperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonicacid, polycondensates of ethylene oxide with fatty alcohols or withfatty acids or with fatty amines, with substituted phenols (preferablyalkylphenols or arylphenols), salts of sulfosuccinic esters, taurinederivatives (preferably alkyl taurates), isethionate derivatives,phosphoric esters of polyethoxylated alcohols or phenols, fatty acidesters of polyols, and derivatives of the compounds containing sulfates,sulfonates and phosphates, for example alkylaryl polyglycol ethers,alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates,lignosulfite waste liquors and methylcellulose. The presence of asurfactant is advantageous if one of the compounds of formula (I) and/orone of the inert carriers is insoluble in water and if the applicationtakes place in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom include dyes such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyessuch as alizarin dyes, azo dyes and metal phthalocyanine dyes, andnutrients and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Additional components which may be present are stabilizers, such as coldstabilizers, preservatives, antioxidants, light stabilizers, or otheragents which improve chemical and/or physical stability. Foam formers orantifoams may also be present.

In addition, the formulations and use forms derived therefrom may alsocomprise, as additional auxiliaries, stickers such ascarboxymethylcellulose and natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further auxiliaries may bemineral and vegetable oils.

It is possible if appropriate for still further auxiliaries to bepresent in the formulations and the use forms derived therefrom.Examples of such additives are fragrances, protective colloids, binders,adhesives, thickeners, thixotropic agents, penetrants, retentionpromoters, stabilizers, sequestrants, complexing agents, humectants,spreaders. In general, the compounds of formula (I) can be combined withany solid or liquid additive commonly used for formulation purposes.

Useful retention promoters include all those substances which reducedynamic surface tension, for example dioctyl sulfosuccinate, or increaseviscoelasticity, for example hydroxypropylguar polymers.

Useful penetrants in the present context are all those substances whichare typically used to improve the penetration of agrochemically activecompounds into plants. Penetrants are defined in this context by theirability to penetrate from the (generally aqueous) application liquorand/or from the spray coating into the cuticle of the plant and hence toincrease the mobility of the active compounds in the cuticle. The methoddescribed in the literature (Baur et al., 1997, Pesticide Science 51,131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulfate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of formula (I), more preferably between 0.01% and95% by weight of the compound of formula (I), most preferably between0.5% and 90% by weight of the compound of formula (I), based on theweight of the formulation.

The content of the compound of formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of formula (I), preferably between 0.00001% and 1% by weight,based on the weight of the use form. The compounds are employed in acustomary manner appropriate for the use forms.

Mixtures

The compounds of formula (I) can also be used in a mixture with one ormore suitable fungicides, bactericides, acaricides, molluscicides,nematicides, insecticides, microbiological agents, beneficial organisms,herbicides, fertilizers, bird repellents, phytotonics, sterilants,safeners, semiochemicals and/or plant growth regulators, in order thus,for example, to broaden the spectrum of action, prolong the period ofaction, enhance the rate of action, prevent repellency or preventevolution of resistance. In addition, active compound combinations ofthis kind can improve plant growth and/or tolerance to abiotic factors,for example high or low temperatures, to drought or to elevated watercontent or soil salinity. It is also possible to improve flowering andfruiting performance, optimize germination capacity and rootdevelopment, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessability of the harvested products.

In addition, the compounds of formula (I) may be present in a mixturewith other active compounds or semiochemicals such as attractants and/orbird repellents and/or plant activators and/or growth regulators and/orfertilizers. Likewise, the compounds of formula (I) can be used toimprove plant properties, for example growth, yield and quality of theharvested material.

In a particular embodiment according to the invention, the compounds offormula (I) are present in formulations or in the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case. All the mixing components mentioned, as the casemay be, may also form salts with suitable bases or acids if they arecapable of doing so on the basis of their functional groups.

Insecticides/Acaricides/Nematicides

The active compounds specified here with their common names are knownand are described for example in “The Pesticide Manual”, 16th ed.,British Crop Protection Council 2012, or can be searched for on theInternet (e.g. http://www.alanwood.net/pesticides). The classificationis based on the IRAC Mode of Action Classification Scheme applicable atthe time of filing of this patent application.

(1) Acetylcholinesterase (AChE) inhibitors, preferably carbamatesselected from alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; ororganophosphates selected from acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos,chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos,demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate,dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur,fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos,isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate,isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos,monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos,pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel blockers, preferablycyclodiene-organochlorines selected from chlordane and endosulfan orphenylpyrazoles (fiproles) selected from ethiprole and fipronil.

(3) Sodium channel modulators, preferably pyrethroids selected fromacrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin,bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin[(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R) isomer],esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin,momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin,pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin,tetramethrin, tetramethrin [(1R) isomer], tralomethrin and transfluthrinor DDT or methoxychlor.

(4) Competitive modulators of the nicotinic acetylcholine receptor(nAChR), preferably neonicotinoids selected from acetamiprid,clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid andthiamethoxam, or nicotine, or sulfoximines selected from sulfoxaflor, orbutenolides selected from flupyradifurone.

(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators,preferably spinosyns selected from spinetoram and spinosad.

(6) Glutamate-gated chloride channel (GluCl) allosteric modulators,preferably avermectins/milbemycins selected from abamectin, emamectinbenzoate, lepimectin and milbemectin.

(7) Juvenile hormone mimetics, preferably juvenile hormone analoguesselected from hydroprene, kinoprene and methoprene or fenoxycarb orpyriproxyfen.

(8) Miscellaneous non-specific (multi-site) inhibitors, preferably alkylhalides selected from methyl bromide and other alkyl halides; orchloropicrin or sulfuryl fluoride or borax or tartar emetic or methylisocyanate generators selected from diazomet and metam.

(9) TRPV channel modulators of chordotonal organs selected frompymetrozine and pyrifluquinazon.

(10) Mite growth inhibitors selected from clofentezine, hexythiazox,diflovidazin and etoxazole.

(11) Microbial disruptors of the insect gut membrane selected fromBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensissubspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, andB.t. plant proteins selected from Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105,Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1/35Ab1.

(12) Inhibitors of mitochondrial ATP synthase, preferably ATP disruptorsselected from diafenthiuron or organotin compounds selected fromazocyclotin, cyhexatin and fenbutatin oxide, or propargite ortetradifon.

(13) Uncouplers of oxidative phosphorylation via disruption of theproton gradient selected from chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinic acetylcholine receptor channel blockers selected frombensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, selected frombistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, selected frombuprofezin.

(17) Moulting disruptors (especially in the case of Diptera) selectedfrom cyromazine.

(18) Ecdysone receptor agonists selected from chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists selected from amitraz.

(20) Mitochondrial complex III electron transport inhibitors selectedfrom hydramethylnon, acequinocyl and fluacrypyrim.

(21) Mitochondrial complex I electron transport inhibitors, preferablyMETI acaricides selected from fenazaquin, fenpyroximate, pyrimidifen,pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers selected from indoxacarband metaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase, preferably tetronic andtetramic acid derivatives selected from spirodiclofen, spiromesifen andspirotetramat.

(24) Mitochondrial complex IV electron transport inhibitors, preferablyphosphines selected from aluminum phosphide, calcium phosphide,phosphine and zinc phosphide, or cyanides selected from calcium cyanide,potassium cyanide and sodium cyanide.

(25) Mitochondrial complex II electron transport inhibitors, preferablybeta-keto nitrile derivatives selected from cyenopyrafen andcyflumetofen, or carboxanilides selected from pyflubumide.

(28) Ryanodine receptor modulators, preferably diamides selected fromchlorantraniliprole, cyantraniliprole and flubendiamide.

(29) Modulators of chordotonal organs (with undefined target structure)selected from flonicamid.

(30) further active compounds selected from afidopyropen, afoxolaner,azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide,bromopropylate, chinomethionat, chloroprallethrin, cryolite,cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol,epsilon metofluthrin, epsilon momfluthrin, flometoquin,fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin,flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide,fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappabifenthrin, kappa tefluthrin, lotilaner, meperfluthrin, paichongding,pyridalyl, pyrifluquinazon, pyriminostrobin, spirobudiclofen,tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,tigolaner, tioxazafen, thiofluoximate, triflumezopyrim and iodomethane;additionally preparations based on Bacillus firmus (1-1582, BioNeem,Votivo), and the following compounds:1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635) (CAS 885026-50-6),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003/106457) (CAS637360-23-7),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494) (CAS 872999-66-1),3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO 2010052161) (CAS 1225292-17-0),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethylcarbonate (known from EP 2647626) (CAS-1440516-42-6),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160) (CAS 792914-58-0), PF1364 (known fromJP2010/018586) (CAS Reg. No. 1204776-60-2),N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(known from WO2012/029672) (CAS 1363400-41-2),(3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one(known from WO2013/144213) (CAS 1461743-15-6),N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide(known from WO2010/051926) (CAS 1226889-14-0),5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide(known from CN103232431) (CAS 1449220-44-3),4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamideand4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide(known from WO 2013/050317 A1) (CAS 1332628-83-7),N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulphinyl]propanamide,(+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulphinyl]propanamide and(−)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulphinyl]propanamide(known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1)(CAS 1477923-37-7),5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulphinyl]-1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS1105672-77-2),3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9);N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO 2012/034403 A1) (CAS 1268277-22-0),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(known from WO 2011/085575 A1) (CAS 1233882-22-8),4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide(known from CN 101715774 A) (CAS 1232543-85-9); cyclopropanecarboxylicacid 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylester (known from CN 103524422 A) (CAS 1542271-46-4);(4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose(known from US 2014/0275503 A1) (CAS 1181213-14-8);8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 1253850-56-4),(8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 933798-27-7),(8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) andN-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide(known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9) andN-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(known from CN 103265527 A) (CAS 1452877-50-7),5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]pyrimidine(known from WO 2013/115391 A1) (CAS 1449021-97-9),3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO 2010/066780 A1, WO 2011/151146 A1) (CAS 1229023-34-0),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione(known from WO 2014/187846 A1) (CAS 1638765-58-8), methyl3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylcarboxylate(known from WO 2010/066780 A1, WO 2011151146 A1) (CAS 1229023-00-0),N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide(known from DE 3639877 A1, WO 2012029672 A1) (CAS 1363400-41-2),[N(E)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide (known from WO 2016005276A1) (CAS 1689566-03-7),[N(Z)]—N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide(CAS 1702305-40-5),3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane(known from WO 2011/105506 A1, WO 2016/133011 A1) (CAS 1332838-17-1).

Fungicides

The active compounds specified herein by their common name are known anddescribed, for example, in “Pesticide Manual” (16th Ed. British CropProtection Council) or can be searched for on the Internet (for example:http://www.alanwood.net/pesticides).

All the mixing components mentioned in classes (1) to (15), as the casemay be, may form salts with suitable bases or acids if they are capableof doing so on the basis of their functional groups. All the fungicidalmixing components mentioned in classes (1) to (15), as the case may be,may include tautomeric forms.

1) Ergosterol biosynthesis inhibitors, for example (1.001)cyproconazole, (1.002) difenocona-zole, (1.003) epoxiconazole, (1.004)fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007)fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010)imazalil, (1.011) imazalil sulphate, (1.012) ipconazole, (1.013)metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016)prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019)pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022)tetraconazole, (1.023) triad-imenol, (1.024) tridemorph, (1.025)triticonazole, (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol(1.029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.032)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.033)(2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.037)1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.038)1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.039)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.044)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.046)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.047)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.048)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.049)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.051)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.052)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.054)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.058)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.059)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.060)5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.061)5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.062)5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.063)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.064)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.065)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.066)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.067)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.068)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.069)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.070)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.071)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(1.072)N′-(4-{[3-(difluoromethoxy)phenyl]sulphanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.073)N′-(4-{3-[(difluoromethyl)sulphanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.074)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(1.075)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(1.076)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.077)N′-{5-bromo-6-1(1S)-1-(3,5-difluorophenyl)ethoxyl-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.078)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.079)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.080)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.081) mefentrifluconazole, (1.082) ipfentrifluconazole.

2) Inhibitors of the respiratory chain in complex I or II, for example(2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004)carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad,(2.008) furametpyr, (2.009) isofetamid, (2.010) isopyrazam(anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimericenantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate1RS,4SR,9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate1RS,4SR,9RS and the anti-epimeric racemate 1RS,4SR,9SR), (2.014)isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam(syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019)pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.023)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.025)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.026)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(2.027)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.028)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.029)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.030)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.031)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.032)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine,(2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.035)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.036)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.037)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.038)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.039)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.041)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.042)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.044)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.045)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(2.046)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.047)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.048)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(2.049)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.050)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.051)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.052)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.053)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.054)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.055)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.056)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.

3) Inhibitors of the respiratory chain at complex III, for example(3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004)coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007)dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadon, (3.010)fenamidon, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013)kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016)picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019)pyraoxystrobin, (3.020) trifloxystrobin, (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.024)(2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.025)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (3.026)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.027)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.029) methyl{5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate.

4) Mitosis and cell division inhibitors, for example (4.001)carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004)fluopicolid, (4.005) pencycuron, (4.006) thiabendazole, (4.007)thiophanate-methyl, (4.008) zoxamide, (4.009)3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(4.011)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine,(4.012)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.013)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.014)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.018)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.019)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.022)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.024)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

5) Compounds having capacity for multi-site activity, for example(5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004)chlorthalonil, (5.005) copper hydroxide, (5.006) copper naphthenate,(5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+)sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013)mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017)copper oxine, (5.018) propineb, (5.019) sulfur and sulfur preparationsincluding calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022)ziram, (5.023)6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3′,4′:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

6) Compounds capable of triggering host defence, for example (6.001)acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004)tiadinil.

7) Amino acid and/or protein biosynthesis inhibitors, for example(7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycinhydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil,(7.006)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

8) ATP production inhibitors, for example (8.001) silthiofam.

9) Cell wall synthesis inhibitors, for example (9.001) benthiavalicarb,(9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005)mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.009)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

10) Lipid and membrane synthesis inhibitors, for example (10.001)propamocarb, (10.002) propamocarb hydrochloride, (10.003)tolclofos-methyl.

11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole,(11.002) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl,(12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004)metalaxyl-M (mefenoxam).

13) Signal transduction inhibitors, for example (13.001) fludioxonil,(13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005)quinoxyfen, (13.006) vinclozolin.

14) Compounds that can act as uncouplers, for example (14.001)fluazinam, (14.002) meptyldinocap.

15) Further compounds, for example (15.001) abscisic acid, (15.002)benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone,(15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid,(15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil,(15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014)fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon,(15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021)oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024)pentachlorophenol and salts, (15.025) phosphonic acid and salts thereof,(15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone),(15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide,(15.031)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.032)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.038)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.041)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.042)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.043)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate, (15.045) 2-phenylphenol and salts thereof, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.047)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.049)4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050)5-amino-1,3,4-thiadiazole-2-thiol, (15.051)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene 2-sulfonohydrazide,(15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.055) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057)phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate,(15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061)tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.062)5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one.

Biological Pesticides as Mixture Components

The compounds of formula (I) can be combined with biological pesticides.

Biological pesticides especially include bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, in particular B. cereus strain CNCM I-1562 or Bacillus firmus,strain 1-1582 (Accession number CNCM I-1582) or Bacillus pumilus, inparticular strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, in particular strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421), Bacillus thuringiensis, in particular B.thuringiensis subspecies israelensis (Serotyp H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, inparticular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyriumminitans, in particular strain CON/M/91-8 (Accession No. DSM-9660),Lecanicillium spp., in particular strain HRO LEC 12, Lecanicilliumlecanii (formerly known as Verticillium lecanii), in particular strainKV01, Metarhizium anisopliae, in particular strain F52 (DSM3884/ATCC90448), Metschnikowia fructicola, in particular strain NRRL Y-30752,Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particularstrain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874),Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL89/030550), Talaromyces flavus, in particular strain V117b, Trichodermaatroviride, in particular strain SC1 (Accession Number CBS 122089),Trichoderma harzianum, in particular T. harzianum rifai T39 (AccessionNumber CNCM I-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Exampleswhich may be mentioned are:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particularBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., oder Gigaspora monosporum, Glomus spp., Laccaria spp.,Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus,Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolii,Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),pyrethrum/pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.

Safeners as Mixture Components

The compounds of the formula (I) can be combined with safeners, forexample benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide,dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim,furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalicanhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya beans, potatoes, sugarbeet, sugar cane, tomatoes, bell peppers, cucumbers, melons, carrots,water melons, onions, lettuce, spinach, leeks, beans, Brassica oleracea(e.g. cabbage) and other vegetable species, cotton, tobacco, oilseedrape, and also fruit plants (the fruits being apples, pears, citrusfruits and grapes). Crop plants may be plants which can be obtained byconventional breeding and optimization methods or by biotechnologicaland genetic engineering methods or combinations of these methods,including the transgenic plants and including the plant cultivars whichare protectable or non-protectable by plant breeders' rights. Plantsshall be understood to mean all development stages such as seed,seedlings, young (immature) plants, up to and including mature plants.Plant parts shall be understood to mean all parts and organs of theplants above and below ground, such as shoot, leaf, flower and root,examples given being leaves, needles, stalks, stems, flowers, fruitbodies, fruits and seeds, and also roots, tubers and rhizomes. Plantparts also include harvested plants or harvested plant parts andvegetative and generative propagation material, for example cuttings,tubers, rhizomes, slips and seeds.

The treatment according to the invention of the plants and parts ofplants with the compounds of formula (I) is effected directly or byallowing the compounds to act on the surroundings, the habitat or thestorage space thereof by the customary treatment methods, for example bydipping, spraying, evaporating, fogging, scattering, painting on,injecting, and, in the case of propagation material, especially in thecase of seeds, also by applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts in accordance with the invention. In a preferred embodiment, wildplant species and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove. Particular preference is given in accordance with the inventionto treating plants of the respective commercially customary plantcultivars or those that are in use. Plant cultivars are understood tomean plants having new properties (“traits”) and which have beenobtained by conventional breeding, by mutagenesis or by recombinant DNAtechniques. They may be cultivars, varieties, biotypes and genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher harvest yields, higher quality and/or higher nutritional value ofthe harvested products, better capability for storage and/orprocessability of the harvested products. Further and particularlyemphasized examples of such properties are increased resistance of theplants to animal and microbial pests, such as insects, arachnids,nematodes, mites, slugs and snails, owing, for example, to toxins formedin the plants, in particular those formed in the plants by the geneticmaterial from Bacillus thuringiensis (for example by the genes CryIA(a),CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb andCryIF and also combinations thereof), and also increased resistance ofthe plants to phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certain activeherbicidal compounds, for example imidazolinones, sulfonylureas,glyphosate or phosphinothricin (for example the “PAT” gene). The geneswhich impart the desired properties (“traits”) in question may also bepresent in combinations with one another in the transgenic plants.Examples of transgenic plants mentioned include the important cropplants, such as cereals (wheat, rice, triticale, barley, rye, oats),maize, soya beans, potatoes, sugar beet, sugar cane, tomatoes, peas andother vegetable species, cotton, tobacco, oilseed rape, and also fruitplants (the fruits being apples, pears, citrus fruits and grapes),particular emphasis being given to maize, soya beans, wheat, rice,potatoes, cotton, sugar cane, tobacco and oilseed rape. Properties(“traits”) which are particularly emphasized are the increasedresistance of the plants to insects, arachnids, nematodes and slugs andsnails.

Crop Protection—Types of Treatment

The plants and plant parts are treated with the compounds of formula (I)directly or by action on their surroundings, habitat or storage spaceusing customary treatment methods, for example by dipping, spraying,atomizing, irrigating, evaporating, dusting, fogging, broadcasting,foaming, painting, spreading, injecting, watering (drenching), dripirrigating and, in the case of propagation material, in particular inthe case of seed, additionally by dry seed treatment, liquid seedtreatment, slurry treatment, by incrusting, by coating with one or morecoats, etc. It is furthermore possible to apply the compounds of formula(I) by the ultra-low volume method or to inject the application form orthe compound of formula (I) itself into the soil.

A preferred direct treatment of the plants is foliar application,meaning that the compounds of formula (I) are applied to the foliage, inwhich case the treatment frequency and the application rate should beadjusted according to the level of infestation with the pest inquestion.

In the case of systemically active compounds, the compounds of formula(I) also access the plants via the root system. The plants are thentreated by the action of the compounds of formula (I) on the habitat ofthe plant. This can be accomplished, for example, by drenching, or bymixing into the soil or the nutrient solution, meaning that the locus ofthe plant (e.g. soil or hydroponic systems) is impregnated with a liquidform of the compounds of the formula (I), or by soil application,meaning that the compounds of the formula (I) according to the inventionare introduced in solid form (e.g. in the form of granules) into thelocus of the plants, or by drip application (frequently also referred toas “chemigation”), meaning that the compounds of the formula (I)according to the invention are introduced via surface or undergrounddrip lines over certain periods of time together with varying amounts ofwater at defined locations in the vicinity of the plants. In the case ofpaddy rice crops, this can also be accomplished by metering the compoundof formula (I) in a solid application form (for example as granules)into a flooded paddy field.

Seed treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvements.Nevertheless, the treatment of seed entails a series of problems whichcannot always be solved in a satisfactory manner. Thus, it is desirableto develop methods for protecting the seed and the germinating plantwhich dispense with, or at least reduce considerably, the additionalapplication of pesticides during storage, after sowing or afteremergence of the plants. It is additionally desirable to optimize theamount of active compound used so as to provide optimum protection forthe seed and the germinating plant from attack by animal pests, butwithout damage to the plant itself by the active compound used. Inparticular, methods for the treatment of seed should also take accountof the intrinsic insecticidal or nematicidal properties ofpest-resistant or -tolerant transgenic plants in order to achieveoptimal protection of the seed and also the germinating plant with aminimum expenditure on pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants from attack by pests,by treating the seed with one of the compounds of formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests further comprises a method in which theseed is treated simultaneously in one operation or sequentially with acompound of formula (I) and a mixing component. It further alsocomprises a method where the seed is treated at different times with acompound of formula (I) and a mixing component.

The invention likewise relates to the use of the compounds of formula(I) for the treatment of seed for protecting the seed and the resultingplant from animal pests.

The invention further relates to seed which has been treated with acompound of formula (I) according to the invention for protection fromanimal pests. The invention also relates to seed which has been treatedsimultaneously with a compound of formula (I) and a mixing component.The invention further relates to seed which has been treated atdifferent times with a compound of formula (I) and a mixing component.In the case of seed which has been treated at different times with acompound of formula (I) and a mixing component, the individualsubstances may be present on the seed in different layers. In this case,the layers comprising a compound of formula (I) and mixing componentsmay optionally be separated by an intermediate layer. The invention alsorelates to seed in which a compound of formula (I) and a mixingcomponent have been applied as part of a coating or as a further layeror further layers in addition to a coating.

The invention further relates to seed which, after the treatment with acompound of formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages that occur when a compound of formula (I) actssystemically is that the treatment of the seed protects not only theseed itself but also the plants resulting therefrom, after emergence,from animal pests. In this way, the immediate treatment of the crop atthe time of sowing or shortly thereafter can be dispensed with.

A further advantage is that the treatment of the seed with a compound offormula (I) can enhance germination and emergence of the treated seed.

It is likewise considered to be advantageous that compounds of formula(I) can especially also be used for transgenic seed.

Furthermore, compounds of formula (I) can be employed in combinationwith compositions of signalling technology, leading to bettercolonization by symbionts such as, for example, rhizobia, mycorrhizaeand/or endophytic bacteria or fungi, and/or to optimized nitrogenfixation.

The compounds of formula (I) are suitable for the protection of seed ofany plant variety which is used in agriculture, in greenhouses, inforests or in horticulture. More particularly, this is the seed ofcereals (for example wheat, barley, rye, millet and oats), maize,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beets (for example sugar beets and fodder beets), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya beans,cotton, canola, oilseed rape, vegetables and rice.

As already mentioned above, the treatment of transgenic seed with acompound of formula (I) is also of particular importance. This involvesthe seed of plants which generally contain at least one heterologousgene which controls the expression of a polypeptide having insecticidaland/or nematicidal properties in particular. The heterologous genes intransgenic seed may originate from microorganisms such as Bacillus,Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus orGliocladium. The present invention is particularly suitable fortreatment of transgenic seed which comprises at least one heterologousgene originating from Bacillus sp. The heterologous gene is morepreferably derived from Bacillus thuringiensis.

In the context of the present invention, the compound of formula (I) isapplied to the seed. The seed is preferably treated in a state in whichit is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. For example, it is possible to use seed which hasbeen harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming. In the case of rice seed, it is alsopossible to use seed which has been soaked, for example in water, untilit reaches a certain stage of the rice embryo (“pigeon breast stage”)which results in stimulation of germination and more uniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activecompounds which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of formula (I) are applied to the seed in theform of a suitable formulation. Suitable formulations and processes forseed treatment are known to the person skilled in the art.

The compounds of formula (I) can be converted to the customaryseed-dressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of formula (I) with customary additives, for example customaryextenders and solvents or diluents, dyes, wetting agents, dispersants,emulsifiers, antifoams, preservatives, secondary thickeners, adhesives,gibberellins, and also water.

Dyes which may be present in the seed-dressing formulations usable inaccordance with the invention are all dyes which are customary for suchpurposes. It is possible to use either pigments, which are sparinglysoluble in water, or dyes, which are soluble in water. Examples includethe dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofagrochemically active compounds. Usable with preference are alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of agrochemically active compounds. Nonionic or anionicdispersants or mixtures of nonionic or anionic dispersants can be usedwith preference. Suitable nonionic dispersants especially includeethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristyrylphenol polyglycol ethers, and the phosphated orsulfated derivatives thereof. Suitable anionic dispersants areespecially lignosulfonates, polyacrylic acid salts andarylsulfonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancescustomary for the formulation of agrochemically active compounds.Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed-dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed-dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz-und Schädlingsbekämpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed-dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats and triticale, and also the seed of maize, rice, oilseed rape,peas, beans, cotton, sunflowers, soya beans and beets, or else a widevariety of different vegetable seed. The seed-dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For the treatment of seed with the seed-dressing formulations usable inaccordance with the invention, or the use forms prepared therefromthrough the addition of water, all mixing units usable customarily forthe seed dressing are useful. Specifically, the procedure in seeddressing is to place the seed into a mixer in batchwise or continuousoperation, to add the particular desired amount of seed-dressingformulations, either as such or after prior dilution with water, and tomix until the formulation is distributed homogeneously on the seed. Ifappropriate, this is followed by a drying operation.

The application rate of the seed-dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds offormula (I) in the formulations and by the seed. The application ratesof the compound of formula (I) are generally between 0.001 and 50 g perkilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.

Animal Health

In the animal health field, i.e. the field of veterinary medicine, thecompounds of formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasite”includes especially helminths and protozoa, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects or acarids.

In the field of veterinary medicine, the compounds of formula (I) havingfavorable endotherm toxicity are suitable for controlling parasiteswhich occur in animal breeding and animal husbandry in livestock,breeding animals, zoo animals, laboratory animals, experimental animalsand domestic animals. They are active against all or specific stages ofdevelopment of the parasites.

Agricultural livestock include, for example, mammals, such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deerand especially cattle and pigs; or poultry such as turkeys, ducks, geeseand especially chickens; or fish or crustaceans, for example inaquaculture; or, as the case may be, insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds; reptiles, amphibians or aquarium fish.

In a specific embodiment, the compounds of formula (I) are administeredto mammals.

In another specific embodiment, the compounds of formula (I) areadministered to birds, namely caged birds or particularly poultry.

Use of the compounds of formula (I) for the control of animal parasitesis intended to reduce or prevent illness, cases of death and reductionsin performance (in the case of meat, milk, wool, hides, eggs, honey andthe like), such that more economical and simpler animal husbandry isenabled and better animal well-being is achievable.

In relation to the field of animal health, the term “control” or“controlling” in the present context means that the compounds of formula(I) are effective in reducing the incidence of the particular parasitein an animal infected with such parasites to an innocuous degree. Morespecifically, “controlling” in the present context means that thecompounds of formula (I) kill the respective parasite, inhibit itsgrowth, or inhibit its proliferation.

The arthropods include, for example, but are not limited to, from theorder of Anoplurida, for example Haematopinus spp., Linognathus spp.,Pediculus spp., Phtirus spp. and Solenopotes spp.;

from the order of Mallophagida and the suborders Amblycerina andIschnocerina, for example Bovicola spp., Damalina spp., Felicola spp.;Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp.,Trinoton spp., Werneckiella spp;

from the order of Diptera and the suborders Nematocerina andBrachycerina, for example Aedes spp., Anopheles spp., Atylotus spp.,Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culexspp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp.,Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp.,Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Luciliaspp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp.,Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp.,Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanusspp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.;from the order of Siphonapterida, for example Ceratophyllus spp.,Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.;from the order of Heteropterida, for example Cimex spp., Panstrongylusspp., Rhodnius spp., Triatoma spp.; and pests and hygiene pests from theorder of Blattarida.

In addition, in the case of the arthropods, mention should be made byway of example, without limitation, of the following Acari:

from the subclass of Acari (Acarina) and the order of Metastigmata, forexample from the family of Argasidae, such as Argas spp., Ornithodorusspp., Otobius spp., from the family of Ixodidae, such as Dermacentorspp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus(Boophilus) spp., Rhipicephalus spp. (the original genus of multi-hostticks); from the order of Mesostigmata, such as Ornithonyssus spp.,Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaelaps spp.,Varroa spp.; from the order of Actinedida (Prostigmata), for exampleAcarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp.,Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergatesspp., Trombicula spp.; and from the order of Acaridida (Astigmata), forexample Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectesspp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectesspp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp.,Tyrophagus spp.

Examples of parasitic protozoa include, but are not limited to:

Mastigophora (Flagellata), such as:

Metamonada: from the order of Diplomonadida, for example Giardia spp.,Spironucleus spp.

Parabasala: from the order of Trichomonadida, for example Histomonasspp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp.,Tritrichomonas spp.

Euglenozoa: from the order of Trypanosomatida, for example Leishmaniaspp., Trypanosoma spp.

Sarcomastigophora (Rhizopoda) such as Entamoebidae, for exampleEntamoeba spp., Centramoebidae, for example Acanthamoeba sp.,Euamoebidae, e.g. Hartmanella sp.

Alveolata such as Apicomplexa (Sporozoa): e.g., B. Cryptosporidium spp.;from the order of Eimeriida, for example Besnoitia spp., Cystoisosporaspp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp.,Sarcocystis spp., Toxoplasma spp.; from the order of Adeleida e.g.Hepatozoon spp., Klossiella spp.; from the order of Haemosporida e.g.Leucocytozoon spp., Plasmodium spp.; from the order of Piroplasmida e.g.Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; from theorder of Vesibuliferida e.g. Balantidium spp., Buxtonella spp.

Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidiumspp., Nosema spp., and furthermore e.g. Myxozoa spp.

The helminths that are pathogenic to humans or animals include, forexample, Acanthocephala, nematodes, Pentastoma and Platyhelminths (e.g.Monogenea, cestodes and trematodes).

Exemplary helminths include, but are not limited to:

Monogenea: e.g.: Dactylogyrus spp., Gyrodactylus spp., Microbothriumspp., Polystoma spp., Troglecephalus spp.;

Cestodes: from the order of Pseudophyllidea, for example: Bothridiumspp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp.,Ligula spp., Schistocephalus spp., Spirometra spp.

From the order of Cyclophyllida, for example: Andyra spp., Anoplocephalaspp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp.,Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp.,Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp.,Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephalaspp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp.,Thysanosoma spp.

Trematodes: from the class of the Digenea, for example: Austrobilharziaspp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchisspp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoeliumspp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp.,Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp.,Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp.,Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeumspp., Leucochloridium spp., Metagonimus spp., Metorchis spp.,Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharziaspp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp.,Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp.,Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

Nematodes: from the order of Trichinellida, for example: Capillariaspp., Trichinella spp., Trichomosoides spp., Trichuris spp.

From the order of Tylenchida, for example: Micronema spp.,Parastrangyloides spp., Strongyloides spp.

From the order of Rhabditina, for example: Aelurostrongylus spp.,Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonemaspp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp.,Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomumspp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp.,Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroidesspp., Globocephalus spp., Graphidium spp., Gyalocephalus spp.,Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagiaspp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirusspp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp.,Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.;Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperiaspp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp.,Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp.,Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylusspp., Syngamus spp., Teladorsagia spp., Trichonema spp.,Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp.,Uncinaria spp.

From the order of Spirurida, for example: Acanthocheilonema spp.,Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculurisspp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp.,Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.;Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp.,Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loaspp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp.,Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp.,Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp.,Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp.,Toxascaris spp., Toxocara spp., Wuchereria spp.

Acanthocephala: from the order of Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order ofMoniliformida, for example: Moniliformis spp.,

From the order of Polymorphida, for example: Filicollis spp.; from theorder of Echinorhynchida, for example Acanthocephalus spp.,Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order of Porocephalida, for example Linguatula spp.

In the veterinary field and in animal husbandry, the compounds offormula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic, metaphylacticor therapeutic.

Thus, one embodiment of the present invention refers to the compounds offormula (I) for use as a medicament.

A further aspect relates to the compounds of formula (I) for use as anantiendoparasitic agent.

A further specific aspect of the invention relates to the compounds offormula (I) for use as an antihelminthic agent, especially for use as anematicide, platyhelminthicide, acanthocephalicide or pentastomicide.

A further specific aspect of the invention relates to the compounds offormula (I) for use as an antiprotozoic agent.

A further aspect relates to the compounds of formula (I) for use as anantiectoparasitic agent, especially an arthropodicide, very particularlyan insecticide or an acaricide.

Further aspects of the invention are veterinary medicine formulationscomprising an effective amount of at least one compound of formula (I)and at least one of the following: a pharmaceutically acceptableexcipient (e.g. solid or liquid diluents), a pharmaceutically acceptableauxiliary (e.g. surfactants), especially a pharmaceutically acceptableexcipient used conventionally in veterinary medicine formulations and/ora pharmaceutically acceptable auxiliary conventionally used inveterinary medicine formulations.

A related aspect of the invention is a method for production of aveterinary medicine formulation as described here, which comprises thestep of mixing at least one compound of formula (I) withpharmaceutically acceptable excipients and/or auxiliaries, especiallywith pharmaceutically acceptable excipients used conventionally inveterinary medicine formulations and/or auxiliaries used conventionallyin veterinary medicine formulations.

Another specific aspect of the invention is veterinary medicineformulations selected from the group of ectoparasiticidal andendoparasiticidal formulations, especially selected from the group ofanthelmintic, antiprotozoic and arthropodicidal formulations, veryparticularly selected from the group of nematicidal,platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidaland acaricidal formulations, according to the aspects mentioned, andmethods for production thereof.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof an effective amount of a compound of formula (I) in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof a veterinary medicine formulation as defined here in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to the use of the compounds of formula (I) in thetreatment of a parasite infection, especially an infection caused by aparasite selected from the group of the ectoparasites and endoparasitesmentioned here, in an animal, especially a nonhuman animal.

In the present context of animal health or veterinary medicine, the term“treatment” includes prophylactic, metaphylactic and therapeutictreatment.

In a particular embodiment, in this way, mixtures of at least onecompound of formula (I) with other active compounds, especially withendo- and ectoparasiticides, are provided for the field of veterinarymedicine.

In the field of animal health, “mixture” means not just that two (ormore) different active compounds are formulated in a common formulationand are correspondingly employed together, but also relates to productscomprising formulations separated for each active compound. Accordingly,when more than two active compounds are to be employed, all activecompounds can be formulated in a common formulation or all activecompounds can be formulated in separate formulations; likewiseconceivable are mixed forms in which some of the active compounds areformulated together and some of the active compounds are formulatedseparately. Separate formulations allow the separate or successiveapplication of the active compounds in question.

The active ingredients specified here by their common names are knownand are described, for example, in the “Pesticide Manual” (see above) orcan be searched for on the Internet (e.g.:http://www.alanwood.net/pesticides).

Illustrative active compounds from the group of the ectoparasiticides asmixing components, without any intention that this should constitute arestriction, include the insecticides and acaricides listed in detailabove. Further usable active compounds are listed below in accordancewith the abovementioned classification based on the current IRAC Mode ofAction Classification Scheme: (1) acetylcholinesterase (AChE)inhibitors; (2) GABA-gated chloride channel blockers; (3) sodium channelmodulators; (4) nicotinic acetylcholine receptor (nAChR) competitivemodulators; (5) nicotinic acetylcholine receptor (nAChR) allostericmodulators; (6) glutamate-gated chloride channel (GluCl) allostericmodulators; (7) juvenile hormone mimetics; (8) miscellaneousnon-specific (multi-site) inhibitors; (9) chordotonal organ modulators;(10) mite growth inhibitors; (12) inhibitors of mitochondrial ATPsynthase, such as ATP disruptors; (13) uncouplers of oxidativephosphorylation via disruption of the proton gradient; (14) nicotinicacetylcholine receptor channel blockers; (15) inhibitors of chitinbiosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1;(17) moulting disruptors (especially in Diptera); (18) ecdysone receptoragonists; (19) octopamine receptor agonists; (21) mitochondrial complexI electron transport inhibitors; (25) mitochondrial complex II electrontransport inhibitors; (20) mitochondrial complex III electron transportinhibitors; (22) voltage-dependent sodium channel blockers; (23)inhibitors of acetyl CoA carboxylase; (28) ryanodine receptormodulators;

active compounds having unknown or non-specific mechanisms of action,e.g. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate,chlordimeform, flubenzimin, dicyclanil, amidoflumet, quinomethionat,triarathene, clothiazoben, tetrasul, potassium oleate, petroleum,metoxadiazone, gossyplur, flutenzine, brompropylate, cryolite;

compounds from other classes, for example butacarb, dimetilan,cloethocarb, phosphocarb, pirimiphos(-ethyl), parathion(-ethyl),methacrifos, isopropyl o-salicylate, trichlorfon, tigolaner, sulprofos,propaphos, sebufos, pyridathion, prothoate, dichlofenthion,demeton-S-methyl sulfone, isazofos, cyanofenphos, dialifos,carbophenothion, autathiofos, aromfenvinfos(-methyl), azinphos(-ethyl),chlorpyrifos(-ethyl), fosmethilan, iodofenphos, dioxabenzofos,formothion, fonofos, flupyrazofos, fensulfothion, etrimfos;

organochlorine compounds, for example camphechlor, lindane, heptachlor;or phenylpyrazoles, e.g. acetoprole, pyrafluprole, pyriprole,vaniliprole, sisapronil; or isoxazolines, e.g. sarolaner, afoxolaner,lotilaner, fluralaner;

pyrethroids, e.g. (cis-, trans-)metofluthrin, profluthrin, flufenprox,flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin,RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin,biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin,clocythrin, cyhalothrin (lambda-), chlovaporthrin, or halogenatedhydrocarbon compounds (HCHs),

neonicotinoids, e.g. nithiazine

dicloromezotiaz, triflumezopyrim

macrocyclic lactones, e.g. nemadectin, ivermectin, latidectin,moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate;milbemycin oxime

triprene, epofenonane, diofenolan;

biologicals, hormones or pheromones, for example natural products, e.g.thuringiensin, codlemone or neem components

dinitrophenols, e.g. dinocap, dinobuton, binapacryl;

benzoylureas, e.g. fluazuron, penfluron,

amidine derivatives, e.g. chlormebuform, cymiazole, demiditraz

beehive varroa acaricides, for example organic acids, e.g. formic acid,oxalic acid.

Illustrative active compounds from the group of the endoparasiticides,as mixing components, include, but are not limited to, activeanthelmintic ingredients and active antiprotozoic ingredients.

The anthelmintic active compounds include but are not limited to thefollowing nematicidally, trematicidally and/or cestocidally activecompounds:

from the class of the macrocyclic lactones, for example: eprinomectin,abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin,latidectin, milbemectin, ivermectin, emamectin, milbemycin;

from the class of the benzimidazoles and probenzimidazoles, for example:oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole,oxfendazole, netobimin, fenbendazole, febantel, thiabendazole,cyclobendazole, cambendazole, albendazole sulfoxide, albendazole,flubendazole;

from the class of the depsipeptides, preferably cyclic depsipeptides,especially 24-membered cyclic depsipeptides, for example: emodepside,PF1022A;

from the class of the tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;

from the class of the imidazothiazoles, for example: butamisole,levamisole, tetramisole;

from the class of the aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;

from the class of the aminoacetonitriles, for example: monepantel;

from the class of the paraherquamides, for example: paraherquamide,derquantel;

from the class of the salicylanilides, for example: tribromsalan,bromoxanide, brotianide, clioxanide, closantel, niclosamide,oxyclozanide, rafoxanide;

from the class of the substituted phenols, for example: nitroxynil,bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan;

from the class of the organophosphates, for example: trichlorfon,naphthalofos, dichlorvos/DDVP, crufomate, coumaphos, haloxon;

from the class of the piperazinones/quinolines, for example:praziquantel, epsiprantel;

from the class of the piperazines, for example: piperazine, hydroxyzine;

from the class of the tetracyclines, for example: tetracycline,chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline;

from various other classes, for example: bunamidine, niridazole,resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquin,mirasan, miracil, lucanthon, hycanthon, hetolin, emetin,diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium,amoscanate, clorsulon.

Active antiprotozoic compounds include, but are not limited to, thefollowing active compounds:

from the class of the triazines, for example: diclazuril, ponazuril,letrazuril, toltrazuril;

from the class of polyether ionophores, for example: monensin,salinomycin, maduramicin, narasin;

from the class of the macrocyclic lactones, for example: milbemycin,erythromycin;

from the class of the quinolones, for example: enrofloxacin,pradofloxacin;

from the class of the quinines, for example: chloroquine;

from the class of the pyrimidines, for example: pyrimethamine;

from the class of the sulfonamides, for example: sulfaquinoxaline,trimethoprim, sulfaclozin;

from the class of the thiamines, for example: amprolium;

from the class of the lincosamides, for example: clindamycin;

from the class of the carbanilides, for example: imidocarb;

from the class of the nitrofurans, for example: nifurtimox;

from the class of the quinazolinone alkaloids, for example:halofuginone;

from various other classes, for example: oxamniquine, paromomycin;

from the class of the vaccines or antigens from microorganisms, forexample: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimerianecatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeriaacervulina, Babesia canis vogeli, Leishmania infantum, Babesia caniscanis, Dictyocaulus viviparus.

All the mixing components mentioned, as the case may be, may also formsalts with suitable bases or acids if they are capable of doing so onthe basis of their functional groups.

Vector Control

The compounds of formula (I) can also be used in vector control. In thecontext of the present invention, a vector is an arthropod, especiallyan insect or arachnid, capable of transmitting pathogens, for exampleviruses, worms, single-cell organisms and bacteria, from a reservoir(plant, animal, human, etc.) to a host. The pathogens can be transmittedeither mechanically (for example trachoma by non-stinging flies) onto ahost or after injection into a host (for example malaria parasites bymosquitoes).

Examples of vectors and the diseases or pathogens they transmit are:

1) Mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of other worms;    -   Aedes: yellow fever, dengue fever, further viral disorders,        filariasis;    -   Simuliidae: transmission of worms, especially Onchocerca        volvulus;    -   Psychodidae: transmission of leishmaniasis        2) Lice: skin infections, epidemic typhus;        3) Fleas: plague, endemic typhus, tapeworms;        4) Flies: sleeping sickness (trypanosomiasis); cholera, other        bacterial diseases;        5) Mites: acariosis, epidemic typhus, rickettsialpox,        tularaemia, Saint Louis encephalitis, tick-borne encephalitis        (TBE), Crimean-Congo haemorrhagic fever, borreliosis;        6) Ticks: borrelioses such as Borrelia bungdorferi sensu lato,        Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella        burnetii), babesioses (Babesia canis canis), ehrlichiosis.

Examples of vectors in the context of the present invention are insects,for example aphids, flies, leafhoppers or thrips, which can transmitplant viruses to plants. Other vectors capable of transmitting plantviruses are spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, Psychodidae such as Phlebotomus, Lutzomyia,lice, fleas, flies, mites and ticks, which can transmit pathogens toanimals and/or humans.

Vector control is also possible if the compounds of formula (I) areresistance-breaking.

Compounds of formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of formula (I) forvector control, for example in agriculture, in horticulture, in forests,in gardens and in leisure facilities, and also in the protection ofmaterials and stored products.

Protection of Industrial Materials

The compounds of formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders of Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of formula (I) are used togetherwith at least one further insecticide and/or at least one fungicide.

In a further embodiment, the compounds of formula (I) take the form of aready-to-use pesticide, meaning that they can be applied to the materialin question without further modifications. Useful further insecticidesor fungicides especially include those mentioned above.

Surprisingly, it has also been found that the compounds of formula (I)can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of formula (I), alone or incombinations with other active compounds, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of formula (I) are suitable for controlling animal pestsin the hygiene sector. More particularly, the invention can be used inthe domestic protection sector, in the hygiene protection sector and inthe protection of stored products, particularly for control of insects,arachnids, ticks and mites encountered in enclosed spaces, for exampledwellings, factory halls, offices, vehicle cabins, animal breedingfacilities. For controlling animal pests, the compounds of formula (I)are used alone or in combination with other active compounds and/orauxiliaries. They are preferably used in domestic insecticide products.The compounds of formula (I) are effective against sensitive andresistant species, and against all developmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or bait stations.

PREPARATION EXAMPLES2-[2-[3,5-Dimethyl-4-oxo-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-ethylsulfonyl-pyrazolo[1,5-a]pyridin-6-yl]cyclopropanecarbonitrile(I-01)

522 mg (0.82 mmol) of2-[3-bromo-2-[3,5-dimethyl-4-oxo-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyrazolo[1,5-a]pyridin-6-yl]cyclopropanecarbonitrile,953.7 mg (8.21 mmol) of sodium methane sulfinate and 23.5 mg (0.12 mmol)of copper(I) iodide were stirred in 6 ml of N,N-dimethylformamide in amicrowave synthesis device (Anton Paar, Monowave 400) for 1 hour at 130°C. A sodium chloride solution was then added to the reaction mixture andthe reaction mixture was extracted with acetic ester. The organic phasewas dried over sodium sulfate and the solvent was then distilled offunder reduced pressure. The residue was purified by columnchromatography purification by preparative HPLC with awater/acetonitrile gradient as eluent.

log P (acidic): 2.80; MH⁺: 505; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 9.10(s, 1H), 8.15 (d, 1H), 7.84 (d, 1H), 7.46 (s, 1H), 4.14 (s, 3H), 3.69(q, 2H), 3.63 (s, 3H), 1.82-1.84 (m, 2H), 1.72-1.74 (m, 2H), 1.20 (t,3H).

2-[3-Bromo-2-[3,5-dimethyl-4-oxo-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl)pyrazolo[1,5-a]pyridin-6-yl]cyclopropanecarbonitrile

205 mg (0.88 mmol) of4-amino-1-methyl-3-(methylamino)-6-(trifluoromethyl)pyridin-2-one, 312mg (0.96 mmol) of3-bromo-6-(1-cyanocyclopropyl)pyrazolo[1,5-a]pyridine-2-carboxylic acidand 261 mg (1.32 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimidehydrochloride (EDCI×HCl) were dissolved in 15 ml of pyridine and stirredat room temperature for 16 h. The solvent was then distilled off underreduced pressure, 15 ml of glacial acetic acid were added to the residueand the mixture was heated at the boil for 12 h. The reaction mixturewas diluted with ethyl acetate and adjusted to pH 6-7 with sodiumbicarbonate. The organic phase was separated off, washed with saturatedsodium chloride solution and dried over sodium sulfate and the solventwas distilled off under reduced pressure.

log P (acidic): 3.37; MH⁺: 491; NMR (400 MHz, D₆-DMSO) δ ppm: 8.94 (s,1H), 7.77 (d, 1H), 7.54 (d, 1H), 7.46 (s, 1H), 4.33 (s, 3H), 3.62 (s,3H), 1.74-1.79 (m, 2H), 1.68-1.71 (m, 2H).

3-Bromo-6-(1-cyanocyclopropyl)pyrazolo[1,5-a]pyridine-2-carboxylic Acid

Under argon and at 0° C., 1.00 g (4.40 mmol) of6-(1-cyanocyclopropyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid and0.862 g (4.84 mmol) of N-bromosuccinimide were dissolved in 200 ml ofchloroform and stirred at 0° C. for 1 h. Water was then added to thereaction mixture, the organic phase was separated off, dried over sodiumsulfate and filtered and the solvent was distilled off under reducedpressure.

log P (acidic): 1.55; MH⁺: 306; ¹H-NMR (400 MHz, DMSO-d₆): δ 13.48 (s,1H), 8.86 (s, 1H), 7.72 (d, 1H), 7.49 (d, 1H), 1.76-1.79 (m, 2H),1.64-1.67 (m, 2H).

6-(1-Cyanocyclopropyl)pyrazolo[1,5-a]pyridine-2-carboxylic Acid

9.00 g (37.3 mmol) of methyl6-(1-cyanocyclopropyl)pyrazolo[1,5-a]pyridine-2-carboxylate and 1.49 g(35.4 mmol) of lithium hydroxide monohydrate were stirred at roomtemperature in a tetrahydrofuran/water mixture (100 ml/150 ml) for 16 h.The organic solvent was then distilled off under reduced pressure, andthe aqueous phase was washed with 100 ml of ethyl acetate and adjustedto pH=4 with 1 N hydrochloride acid. The precipitated solid was filteredoff and dried under reduced pressure.

¹H-NMR (400 MHz, DMSO-d₆): δ 13.00 (br. s, 1H), 8.78 (s, 1H), 7.79 (d,1H), 7.32 (d, 1H), 7.07 (s, 1H), 1.74 (m, 2H), 1.62 (m, 2H).

Methyl 6-(1-Cyanocyclopropyl)pyrazolo[1,5-a]pyridine-2-carboxylate

30 g (111 mmol) of a 0.4 molar solution of methyl(E)-2-azido-3-[5-(1-cyanocyclopropyl)-2-pyridyl]prop-2-enoate inmesitylene was heated at reflux for 1 h, allowed to cool and then cooledto 0° C. for 1 h. The precipitated crystalline product was filtered off,stirred in an ethyl acetate/hexane mixture (1:20) overnight, filteredoff and dried under reduced pressure. The product was used withoutfurther purification for the next step.

Methyl (E)-2-azido-3-[5-(1-cyanocyclopropyl)-2-pyridyl]prop-2-enoate

Over 30 min, a solution of 17.6 g (326 mmol) of sodium methoxide in 200ml of methanol was slowly added dropwise to a solution, cooled to −10 to−15° C., of 50.0 g (290 mmol) of6-formyl-3-pyridyl)cyclopropanecarbonitrile and 36.8 g (320 mmol) ofmethyl azidoacetate in 350 ml of methanol, keeping the reactiontemperature at −10° C. After the addition, the temperature was allowedto slowly warm to 0° C. and the reaction was kept at this temperaturefor a further 2 h. During this time, the product began to precipitate asa fine precipitate. The reaction flask was fitted with a bubble counterand the reaction was stirred with ice bath cooling overnight. Theresulting suspension was then added to a mixture of 2 kg of ice and 400g of solid ammonium chloride, stirred until the ice was melted andfiltered off.

The filter cake was washed with cold water, dried under reduced pressureand dissolved in 600 ml of dichloromethane. The organic phase was driedover magnesium sulfate and filtered through silica gel and the residuewas washed with 200 ml of dichloromethane. The combined organic phaseswere concentrated and the residue was used without further purificationfor the next step.

Analytical Determinations

The analytical determination methods described below apply to allstatements in the entire document unless the respective analyticaldetermination method is specially described in the relevant textpassage.

Mass Spectrometry

The determination of [M+H]⁺ or M⁻ by LC-MS under acidic chromatographicconditions was carried out using 1 ml of formic acid per litre ofacetonitrile and 0.9 ml of formic acid per litre of Millipore water asmobile phases. The Zorbax Eclipse Plus C18 50 mm*2.1 mm, 1.8 μm columnwas used at a column oven temperature of 55° C.

Instruments:

LC-MS3: Waters UPLC with SQD2 mass spectrometer and SampleManager samplechanger. Linear gradient from 0.0 to 1.70 minutes from 10% acetonitrileto 95% acetonitrile, from 1.70 to 2.40 minutes constant 95%acetonitrile, flow rate 0.85 ml/min.

LC-MS6 and LC-MS7: Agilent 1290 LC, Agilent MSD mass spectrometer, HTSPAL sample changer. Linear gradient from 0.0 to 1.80 minutes from 10%acetonitrile to 95% acetonitrile, from 1.80 to 2.50 minutes constant 95%acetonitrile, flow rate 1.0 ml/min.

The determination of [M+H]⁺ by LC-MS under neutral chromatographicconditions was carried out using acetonitrile and Millipore water with79 mg/l ammonium carbonate as mobile phases.

Instruments:

LC-MS4: Waters IClass Acquity with QDA mass spectrometer and FTN samplechanger (column Waters Acquity 1.7 μm 50 mm*2.1 mm, column oventemperature 45° C.). Linear gradient from 0.0 to 2.10 minutes from 10%acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95%acetonitrile, flow rate 0.7 ml/min.

LC-MS5: Agilent 1100 LC system with MSD mass spectrometer and HTS PALsample changer (column: Zorbax XDB C18 1.8 μm 50 mm*4.6 mm, column oventemperature 55° C.). Linear gradient from 0.0 to 4.25 minutes from 10%acetonitrile to 95% acetonitrile, from 4.25 to 5.80 minutes constant 95%acetonitrile, flow rate 2.0 ml/min.

In all cases, the retention time indices were determined from acalibration measurement of a homologous series of straight-chainalkan-2-ones having 3 to 16 carbons, where the index of the firstalkanone was set to 300, the index of the last alkanone was set to 1600and linear interpolation was carried out between the values ofsuccessive alkanones.

log P Values

The log P values were determined according to EEC Directive 79/831 AnnexV.A8 by HPLC (high-performance liquid chromatography) on areversed-phase column (C18) using the following methods:

^([a]) The log P value is determined by LC-UV measurement in the acidicrange using 0.9 ml/l formic acid in water and 1.0 ml/l formic acid inacetonitrile as mobile phases (linear gradient from 10% acetonitrile to95% acetonitrile).

^([b]) The log P value is determined by LC-UV measurement in the neutralrange using 79 mg/l ammonium carbonate in water and acetonitrile asmobile phases (linear gradient from 10% acetonitrile to 95%acetonitrile).

Calibration was carried out using a homologous series of straight-chainalkan-2-ones (having 3 to 16 carbon atoms) with known log P values. Thevalues between successive alkanones are determined by linear regression.

¹H NMR Spectra

The ¹H NMR spectra were measured with a Bruker Avance III 400 MHzspectrometer fitted with a 1.7 mm TCI sample head usingtetramethylsilane as standard (0.00 ppm), of solutions in the solventsCD₃CN, CDCl₃ or d₆-DMSO. Alternatively, a Bruker Avance III 600 MHzspectrometer fitted with a 5 mm CPNMP sample head or a Bruker Avance NEO600 MHz spectrometer fitted with a 5 mm TCI sample head was employed forthe measurements. In general, the measurements were carried out at asample head temperature of 298 K. If other measurement temperatures wereused, this is specifically mentioned.

NMR Peak Lists Method

The ¹H NMR data of selected examples are represented in the form of ¹HNMR peak lists. For each signal peak, first the δ value in ppm and thenthe signal intensity in round brackets are listed. The δ value/signalintensity number pairs for different signal peaks are listed withseparation from one another by semicolons.

The peak list for one example therefore has the form:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed representation of a ¹H NMR spectrum in cm and shows thetrue ratios of the signal intensities. In the case of broad signals,several peaks or the middle of the signal and the relative intensitythereof may be shown in comparison to the most intense signal in thespectrum.

Calibration of the chemical shift of ¹H NMR spectra is accomplishedusing tetramethylsilane or the chemical shift of the solvent if thesample does not contain any tetramethylsilane. Accordingly, in certaincases the ¹H NMR peak lists may comprise the tetramethylsilane peak.

The ¹H NMR peak lists are equivalent to conventional ¹H NMRrepresentations and thus usually contain all peaks listed in aconventional ¹H NMR interpretation.

In addition, like conventional ¹H NMR representations, they may showsolvent signals, signals of stereoisomers of the compounds according tothe invention which are optionally provided by the invention, and/orpeaks of impurities.

NMR solvent signals, the tetramethylsilane peak and the water signal inthe solvent in question are excluded from the calibration of therelative intensity since their stated intensity values can be very high.

The peaks of (stereo)isomers of the compounds of the invention and/orpeaks of impurities usually have a lower intensity on average than thepeaks of the compounds of the invention (for example at a purity of>90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in this case to identifyreproduction of a preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the compounds according to theinvention by known methods (MestreC, ACD simulation, but also withempirically evaluated expected values) can, if required, identify thepeaks of the compounds of the invention, optionally using additionalintensity filters. This identification is equivalent to the relevantpeak listing in conventional 1H NMR interpretation.

In the JCAMP file, the solvent employed, the measuring frequency of thespectrometer and the spectrometer model can be found using the parameter“solvent”, “observe frequency” and “spectrometer/data system”,respectively.

¹³C NMR data are stated analogously to the ¹H NMR data as peak listsusing broadband-decoupled ¹³C NMR spectra. Here, too, NMR solventsignals and tetramethylsilane are excluded from the calibration of therelative intensity since these signals may have very high intensityvalues.

Further details on ¹H NMR peak lists can be found in: “Citation of NMRPeaklist Data within Patent Applications” in Research DisclosureDatabase Number 564025.

The compounds listed in Table 1 were prepared as described above oranalogously thereto.

TABLE 1 Example Structure I-01

I-01: ¹H-NM (600.1 MHz, d₆-DMSO): δ = 9.0922 (3.3); 9.0915 (3.3); 8.1634(2.2); 8.1485 (2.4); 8.1476 (2.5); 7.8539 (1.9); 7.8513 (1.9); 7.8383(1.7); 7.8356 (1.8); 7.4698 (0.3); 7.4570 (4.7); 4.3371 (1.0); 4.1422(16.0); 3.7057 (1.0); 3.6935 (3.3); 3.6812 (3.4); 3.6690 (1.1); 3.6273(9.4); 3.3230 (27.8); 2.5436 (1.4); 2.5251 (0.5); 2.5222 (0.7); 2.5190(0.8); 2.5071 (26.1); 2.5043 (34.2); 2.5015 (26.6); 1.8368 (1.1); 1.8276(3.1); 1.8230 (3.7); 1.8154 (1.6); 1.7370 (1.6); 1.7289 (3.5); 1.7244(3.4); 1.7150 (1.1); 1.2185 (0.4); 1.2080 (3.8); 1.1958 (7.8); 1.1835(3.5); −0.0001 (1.1) I-02

I-02: ¹H-NMR (400.2 MHz, d₆-DMSO): δ = 9.0692 (3.0); 8.3157 (1.5);8.1901 (2.0); 8.1668 (2.2); 7.7966 (1.7); 7.7928 (1.8); 7.7735 (1.6);7.7701 (1.7); 7.4595 (4.6); 4.2234 (7.2); 4.1376 (16.0); 3.7082 (1.0);3.6894 (3.2); 3.6708 (3.4); 3.6519 (1.1); 3.6311 (8.1); 3.3233 (619.5);3.2724 (0.5); 2.6749 (5.2); 2.6705 (7.2); 2.6661 (5.5); 2.6293 (0.6);2.5980 (0.7); 2.5237 (25.9); 2.5101 (424.9); 2.5060 (855.5); 2.5016(1131.3); 2.4971 (858.7); 2.3328 (4.9); 2.3284 (6.9); 2.3240 (5.2);2.0742 (0.4); 1.2330 (0.4); 1.2142 (3.4); 1.1959 (7.7); 1.1773 (3.4);0.1458 (5.6); 0.0598 (0.3); 0.0077 (50.6); −0.0003 (1193.9); −0.1497(5.6) I-03

I-03: ¹H-NMR (600.1 MHz, d₆-DMSO): δ = 8.8934 (3.1); 8.0222 (2.1);8.0066 (2.2); 7.5168 (1.7); 7.5145 (1.7); 7.5012 (1.6); 7.4989 (1.6);7.4464 (4.6); 4.3635 (0.4); 4.3318 (0.4); 4.1574 (0.5); 4.1269 (16.0);3.6644 (1.1); 3.6521 (3.4); 3.6397 (3.7); 3.6283 (9.4); 3.3186 (187.6);2.6140 (1.0); 2.5229 (1.9); 2.5199 (2.3); 2.5168 (2.2); 2.5049 (103.6);2.5019 (141.4); 2.4990 (104.3); 2.3857 (0.9); 2.1373 (0.6); 2.1315(0.7); 2.1234 (1.2); 2.1150 (0.7); 2.1095 (0.6); 2.1009 (0.3); 1.3534(0.4); 1.3415 (0.7); 1.3295 (0.4); 1.1923 (3.7); 1.1800 (7.9); 1.1677(3.6); 1.0597 (0.7); 1.0518 (2.0); 1.0485 (2.2); 1.0379 (2.1); 1.0345(2.1); 1.0274 (0.9); 0.8831 (0.8); 0.8753 (2.5); 0.8727 (2.4); 0.8675(2.2); 0.8644 (2.7); 0.8566 (0.7); 0.0053 (0.9); −0.0001 (28.1)

USE EXAMPLES

Ctenocephalides felis—Oral Test

Solvent: dimethyl sulfoxide

To produce a suitable active compound formulation, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution withcitrated cattle blood gives the desired concentration.

About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into achamber which is closed at the top and bottom with gauze. A metalcylinder whose bottom end is closed with parafilm is placed onto thechamber. The cylinder contains the blood/active compound formulation,which can be imbibed by the fleas through the parafilm membrane.

After 2 days, the kill in % is determined. 100% means that all of thefleas have been killed; 0% means that none of the fleas have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 97% at an application rate of 100 ppm:I-01.

Meloidogyne incognita Test

Solvent: 125.0 parts by weight of acetone

To produce a suitable active compound formulation, 1 part by weight ofactive compound is mixed with the stated amount of solvent and theconcentrate is diluted to the desired concentration with water.

Vessels are filled with sand, active compound solution, an egg/larvaesuspension of the southern root-knot nematode (Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop.The galls develop on the roots.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls were found; 0% means thatthe number of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 ppm:I-01.

Diabrotica balteata—Spray Test

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved using the stated parts by weight of solventand made up with water containing an emulsifier concentration of 1000ppm until the desired concentration is attained. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Pre-swollen wheat grains (Triticum aestivum) are incubated in amultiwell plate filled with agar and a little water for one day (5 seedgrains per cavity). The germinated wheat grains are sprayed with anactive compound preparation of the desired concentration. Subsequently,each cavity is infected with 10-20 beetle larvae of Diabrotica balteata.

After 7 days, the efficacy in % is determined. 100% means that all wheatplants have grown as in the untreated, uninfected control; 0% means thatno wheat plant has grown.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 160μg/cavity: 1-03.

Myzus persicae—Spray Test

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved using the stated parts by weight of solventand made up with water containing an emulsifier concentration of 1000ppm until the desired concentration is attained. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound formulation of the desired concentration.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 g/ha:1-03.

Myzus persicae—Oral Test

Solvent: 100 parts by weight of acetone

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water until the desired concentration isattained.

50 μl of the active compound preparation are transferred into microtitreplates and made up to a final volume of 200 μl with 150 μl of IPL41insect medium (33%+15% sugar). Subsequently, the plates are sealed withparafilm, which a mixed population of green peach aphids (Myzuspersicae) within a second microtitre plate is able to puncture andimbibe the solution through.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 4 ppm: I-01,I-02, I-03.

Spodoptera frugiperda—Spray Test

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved using the stated parts by weight of solventand made up with water containing an emulsifier concentration of 1000ppm until the desired concentration is attained. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Leaf discs of maize (Zea mays) are sprayed with an active compoundformulation of the desired concentration and, after drying, populatedwith caterpillars of the fall armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that all thecaterpillars have been killed; 0% means that no caterpillar has beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-02, I-03.

The invention claimed is:
 1. A compound of formula (I)

in which B₁ represents C(R¹¹), B₂ represents C(R¹²), B₃ representsC(R¹³) and B₄ represents C(R¹⁴) and R¹ represents (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl, (C₁-C₆)-hydroxyalkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,(C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl,(C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyl,(C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,(C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,halo-(C₃-C₈)-cycloalkyl, amino, (C₁-C₆)-alkylamino,di-(C₁-C₆)-alkyl-amino, (C₃-C₈)-cycloalkylamino,(C₁-C₆)-alkylcarbonylamino, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonylamino,aminosulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl ordi-(C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl, R¹¹, R¹², R¹³, R¹⁴independently of one another represent hydrogen, cyano, halogen, nitro,hydroxy, amino, SCN, tri-(C₁-C₆)-alkylsilyl, (C₃-C₈)-cycloalkyl,(C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,halo-(C₃-C₈)-cycloalkyl, cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-haloalkyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,(C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,(C₁-C₆)-alkylhydroxyimino, (C₁-C₆)-alkoxyimino,(C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,(C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,(C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl,(C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-alkylcarbonyl, (C₃-C₈)-cycloalkylcarbonyl,(C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₆)-alkylaminothiocarbonyl, (C₂-C₆)-alkenylaminocarbonyl,di-(C₂-C₆)-alkenylaminocarbonyl, (C₃-C₈)-cycloalkylaminocarbonyl,(C₁-C₆)-alkylsulfonylamino, (C₁-C₆)-alkylamino, aminosulfonyl,(C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,(C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,(C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl ((C₁-C₆)-alkylcarbonylamino)or NHCO—(C₃-C₈)-cycloalkyl ((C₃-C₈)-cycloalkylcarbonylamino), orrepresent aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand/or where possible substituents are in each case as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri-(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di-(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino, where at most threeof the radicals R¹¹, R¹², R¹³ and R¹⁴ represent a substituent differentfrom hydrogen, R⁴, R⁵ independently of one another represent(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,(C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,(C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl or(C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl and R⁶ represents hydrogen, cyano,halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,(C₃-C₆)-cycloalkyl, cyano-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxyimino,(C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylsulfinyl,(C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfonyloxy,(C₁-C₄)-alkylcarbonyl, (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl,(C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,(C₁-C₄)-alkylsulfonylamino, (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,aminosulfonyl, (C₁-C₄)-alkylaminosulfonyl ordi-(C₁-C₄)-alkylaminosulfonyl and n represents 0, 1 or
 2. 2. Thecompound of formula (I) as claimed in claim 1, wherein B₁ represents CH,B₂ represents C(R¹²), B₃ represents C(R¹³) and B₄ represents CH and R¹represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,halo-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl or(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, R¹², R¹³ independently of oneanother represent hydrogen, cyano, halogen, hydroxy, amino, SCN,(C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,(C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,(C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,(C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-haloalkylsulfonyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-alkylcarbonyl, (C₃-C₈)-cycloalkylcarbonyl,(C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₆)-alkylaminothiocarbonyl, (C₂-C₆)-alkenylaminocarbonyl,di-(C₂-C₆)-alkenylaminocarbonyl, (C₃-C₈)-cycloalkylaminocarbonyl,(C₁-C₆)-alkylsulfonylamino, (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino,aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,di-(C₁-C₆)-alkylaminosulfonyl, (C₁-C₆)-alkylsulfoximino,aminothiocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylamino,NHCO—(C₁-C₆)-alkyl ((C₁-C₆)-alkylcarbonylamino) orNHCO—(C₃-C₈)-cycloalkyl ((C₃-C₈)-cycloalkylcarbonylamino), or representaryl or hetaryl, each of which is optionally mono- or polysubstituted byidentical or different substituents, where (in the case of hetaryl) atleast one carbonyl group may optionally be present and/or where possiblesubstituents are in each case as follows: cyano, carboxyl, halogen,acetyl, hydroxy, amino, SCN, (C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkyl,halo-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio,(C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonylor (C₁-C₆)-haloalkylsulfonyl, R⁴, R⁵ independently of one anotherrepresent (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,(C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,(C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₃-C₆)-cycloalkyl,(C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl or halo-(C₃-C₆)-cycloalkyl, R⁶represents hydrogen, cyano, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-haloalkynyl, (C₃-C₆)-cycloalkyl, cyano-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl,(C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl or(C₁-C₄)-haloalkylsulfonyl and n represents 0, 1 or
 2. 3. The compound offormula (I) as claimed in claim 1, wherein B₁ represents CH, B₂represents C(R¹²), B₃ represents C(R¹³) and B₄ represents CH and R¹represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₁-C₆)-haloalkenyl, (C₁-C₆)-alkynyl, (C₂-C₆)-haloalkynyl or(C₃-C₈)-cycloalkyl, R¹², R¹³ independently of one another representhydrogen, cyano, halogen, hydroxy, amino, SCN, (C₃-C₈)-cycloalkyl,(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,(C₁-C₆)-hydroxyalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,(C₁-C₆)-alkynyl, (C₁-C₆)-haloalkynyl, (C₁-C₆)-alkoxy,(C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy, (C₁-C₆)-alkylthio,(C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl,(C₁-C₆)-alkylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl,(C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkylcarbonyl,(C₃-C₈)-cycloalkylcarbonyl, (C₁-C₆)-alkylthiocarbonyl,(C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylaminocarbonyl,(C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,(C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,aminothiocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylamino,NHCO—(C₁-C₆)-alkyl ((C₁-C₆)-alkylcarbonylamino) orNHCO—(C₃-C₈)-cycloalkyl ((C₃-C₈)-cycloalkylcarbonylamino), R⁴, R⁵independently of one another represent (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-haloalkynyl or (C₃-C₆)-cycloalkyl, R⁶ represents hydrogen,cyano, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl,cyano-(C₃-C₆)-cycloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,(C₁-C₄)-haloalkylsulfinyl or (C₁-C₄)-haloalkylsulfonyl and n represents0, 1 or
 2. 4. A compound of formula (Ia)

where R¹ represents (C₁-C₄)-alkyl or (C₃-C₆)-cycloalkyl, R¹², R¹³independently of one another represent hydrogen, cyano, halogen,hydroxy, (C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,halo-(C₃-C₈)cycloalkyl, cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-cyanoalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,(C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylsulfinyl,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl,(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-haloalkylsulfonyl,(C₁-C₆)-alkylcarbonyl, (C₃-C₈)-cycloalkylcarbonyl,(C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylaminocarbonyl,(C₁-C₆)-alkylamino, aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,di-(C₁-C₆)-alkylaminosulfonyl, (C₃-C₈)-cycloalkylamino,NHCO—(C₁-C₆)-alkyl ((C₁-C₆)-alkylcarbonylamino) orNHCO—(C₃-C₈)-cycloalkyl ((C₃-C₈)-cycloalkylcarbonylamino), R⁴, R⁵independently of one another represent (C₁-C₄)-alkyl or(C₃-C₆)-cycloalkyl, R⁶ represents hydrogen, halogen, (C₁-C₄)-haloalkyl,cyano-(C₃-C₆)-cycloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,(C₁-C₄)-haloalkylsulfinyl or (C₁-C₄)-haloalkylsulfonyl and n represents0, 1 or
 2. 5. The compound of formula (Ia) as claimed in claim 4,wherein R¹ represents (C₁-C₄)-alkyl, R¹² represents (C₁-C₄)-cyanoalkylor (C₃-C₆)-cycloalkyl which is optionally monosubstituted by cyano, R¹³represents hydrogen, R⁴, R⁵ independently of one another represent(C₁-C₄)-alkyl, R⁶ represents (C₁-C₄)-haloalkyl and n represents
 2. 6.The compound of formula (Ia) as claimed in claim 4, wherein R¹represents ethyl, R¹² represents cyanocyclopropyl, cyclopropyl orcyanomethyl, R¹³ represents hydrogen, R⁴, R⁵ represent methyl, R⁶represents trifluoromethyl and n represents
 2. 7. The compound offormula (Ia′)

where R¹², R¹³ independently of one another represent hydrogen, cyano,halogen, hydroxy, amino, SCN, (C₃-C₈)-cycloalkyl,(C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,halo-(C₃-C₈)-cycloalkyl, cyano-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-cyanoalkyl, (C₁-C₆)-hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,(C₁-C₆)-cyanoalkoxy, (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino,(C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfonyl, (C₃-C₅)-cycloalkylsulfonyl,(C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfonyloxy, (C₁-C₆)-alkylcarbonyl,(C₃-C₈)-cycloalkylcarbonyl, (C₁-C₆)-alkylthiocarbonyl,(C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,(C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,di-(C₁-C₈)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,(C₁-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,(C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,(C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,(C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,(C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl ((C₁-C₆)-alkylcarbonylamino)or NHCO—(C₃-C₈)-cycloalkyl ((C₃-C₈)-cycloalkylcarbonylamino), orrepresent aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand/or where possible substituents are in each case as follows: cyano,carboxyl, halogen, acetyl, hydroxy, amino, SCN, (C₃-C₈)-cycloalkyl,(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,(C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,(C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulfinyl,(C₁-C₆)-alkylsulfonyl or (C₁-C₆)-haloalkylsulfonyl, R⁴, R⁵ independentlyof one another represent (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,(C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₃-C₆)-cycloalkyl,(C₁-C₄)-alkyl-(C₃-C₈)-cycloalkyl or halo-(C₃-C₆)-cycloalkyl, R⁶represents hydrogen, cyano, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-haloalkynyl, (C₃-C₆)-cycloalkyl, cyano-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl,(C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl or(C₁-C₄)-haloalkylsulfonyl and n represents 0, 1 or
 2. 8. The compound offormula (Ia) as claimed in claim 4, wherein R¹³ represents hydrogen. 9.An agrochemical formulation comprising one or more compounds of formula(I), as claimed in claim 1 and one or more extenders and/or surfactants.10. The agrochemical formulation as claimed in claim 9, additionallycomprising a further agrochemically active compound.
 11. A method ofcontrolling one or more animal pests, comprising allowing a compound offormula (I) as claimed in claim 1 or an agrochemical formulation thereofto act on the animal pests and/or a habitat thereof.
 12. A productcomprising one or more compounds of formula (I), as claimed in claim 1or an agrochemical formulation thereof for controlling one or moreanimal pests.